Tretinoin

Identification

Summary

Tretinoin is a vitamin A derivative used to treat acne vulgaris and certain types of promyelocytic leukemia, as well as various skin conditions in over-the-counter medications.

Brand Names
Altreno, Atralin, Biacna, Refissa, Renova, Retin-A, Stieva-A, Tri-luma, Twyneo, Veltin, Vesanoid, Ziana
Generic Name
Tretinoin
DrugBank Accession Number
DB00755
Background

Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol).1 It is an oxidation product in the physiological pathway of vitamin A metabolism.5 In human circulation, tretinoin is normally found at very low concentrations, approximately 4 to 14 nmol/L.5 Tretinoin exhibits anti-inflammatory, antineoplastic, antioxidant, and free radical-scavenging activities.5 It has been used in dermatology for many years to treat various skin conditions ranging from acne to wrinkles 1,11 and activates nuclear receptors to regulate epithelial cell growth and differentiation.1,2,3 Tretinoin is given orally to treat acute promyelocytic leukemia 13 and topically to treat skin conditions such as acne.15,12,14

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 300.442
Monoisotopic: 300.208930142
Chemical Formula
C20H28O2
Synonyms
  • (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
  • 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL)
  • Acide retinoique
  • all trans Retinoic acid
  • all trans-Retinoic acid
  • all-(E)-Retinoic acid
  • all-trans-beta-Retinoic acid
  • all-trans-Retinoic acid
  • all-trans-Tretinoin
  • all-trans-Vitamin A acid
  • all-trans-Vitamin A1 acid
  • ATRA
  • beta-Retinoic acid
  • Retinoic acid
  • Retionic acid
  • trans-Retinoic acid
  • Tretin M
  • Tretinoin
  • Tretinoina
  • Trétinoïne
  • Tretinoinum
  • Vitamin A acid
External IDs
  • AGN 100335
  • NSC-122758
  • Ro 1-5488

Pharmacology

Indication

Oral tretinoin is indicated for induction of remission in adults and pediatric patients one year of age and older with acute promyelocytic leukemia (APL), characterized by the presence of t(15;17) translocation or presence of PML/RARα gene expression and who are refractory to or who have relapsed from anthracycline chemotherapy or for whom anthracycline-based chemotherapy is contraindicated.13

Topical tretinoin is also indicated alone 15 or in combination with benzoyl peroxide 12 or clindamycin 14 for the treatment of acne vulgaris. It is also used in prescription and over-the-counter for treating various skin conditions such as melasma,16 hyperpigmentation,1 and photoaging 10 alone or in combination with other drugs.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcne vulgaris••••••••••••
Used in combination to treatAcne vulgarisCombination Product in combination with: Benzoyl peroxide (DB09096)•••••••••••••••••
Used in combination to treatAcne vulgarisCombination Product in combination with: Clindamycin (DB01190)••••••••••••
Used in combination to treatAlopeciaCombination Product in combination with: Minoxidil (DB00350)••••••••••••••••••••
Used in combination to treatCornification and dystrophic skin disordersCombination Product in combination with: Urea (DB03904)•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tretinoin is a vitamin A derivative that promotes cell production, proliferation, and differentiation. When used topically, tretinoin regulates epidermal cell turnover and collagen production. It also prevents collagen loss, reduces inflammation, and blocks the induction of matrix metalloproteinase (MMP), which are enzymes that disrupt collagen and elastic fibres.1,2,3,10 In short-term and long-term studies, topical application of tretinoin at doses ranging from 0.001% to 0.1% was associated with improvements in clinical signs of photoaging and fine wrinkles, increased epidermal thickness, compaction of the stratum corneum, and decreased melanin content.4,10,11,7 It also improved melanocyte differentiation and distribution, promotion of epidermal hyperplasia, and angiogenesis.7

Tretinoin exhibits antineoplastic activities when given orally.13 Tretinoin was shown to induce differentiation in tumour cells.6 It induced cytodifferentiation and decreased acute promyelocytic leukemia (APL) cell proliferation in culture and in vivo. In patients with APL, tretinoin promoted the initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission.13

Mechanism of action

The exact mechanism of action of tretinoin in skin conditions and acute promyelocytic leukemia (APL) has not been fully elucidated; however, several proposed mechanisms exist. Tretinoin is believed to exert its pharmacological actions by binding to and activating two types of nuclear receptors - retinoic acid receptors (RARs) alpha, beta, and gamma and retinoid X receptors (RXRs). In the human skin, RARs (especially RAR-alpha) form heterodimers with RXR to act as inducible transcription regulators of genes involved in cell differentiation by binding to retinoic acid response elements.9,11 Tretinoin binds to RXRs to promote epidermal proliferation. It also blocks the actions of inflammatory mediators, enhancing procollagen production and collagen type I and III formations.1,2,3,7 Some animal and human studies suggest that tretinoin induces the expression of transforming growth factor beta (TGF-β), which stimulates the transcription of several types of collagen messenger RNA. Collagen formation curtails further solar UV-induced skin damage and aging processes.7

Acne is associated with abnormal follicular formation from excessive keratinization of epithelial cells. Tretinoin promotes cornified cell detachment and enhances keratinocyte shedding. It also stimulates mitotic activity and loosely-adherent corneocyte turnover to expel comedo contents, reducing microcomedo precursor lesions of acne vulgaris.1,12 Tretinoin may reduce epidermal melanin and pigmentation by increasing keratinocyte turnover and reducing tyrosinase activity.3,10

RAR-alpha and -beta have also been implicated in APL.9 APL is characterized by a t(15;17) chromosomal translocation, which fuses the promyelocytic myeloid leukemia (PML) gene with the RAR-alpha gene.5,6 The resulting PML-RAR-alpha fusion protein plays a role in the pathogenesis of APL by aberrating promyelocyte differentiation. The PML-RAR-alpha fusion protein is found to be predominant in leukemic cells, exerting a dominant negative effect on RAR, RXR and PML function.5 Tretinoin induces terminal differentiation in hemopoietic precursor cell lines and APL cells.6 Tretinoin is believed to promote caspase-mediated cleavage and proteasome-dependent degradation to cause apoptosis and degradation of the PML-RAR-alpha fusion protein.1 It may also convert the fusion protein from a transcription repressor to an activator.1

TargetActionsOrganism
ARetinoic acid receptor alpha
agonist
Humans
ARetinoic acid receptor beta
agonist
Humans
ARetinoic acid receptor gamma
agonist
Humans
URetinoic acid receptor RXR-alpha
agonist
Humans
ARetinoic acid receptor RXR-beta
agonist
Humans
ARetinoic acid receptor RXR-gamma
agonist
Humans
UCellular retinoic acid-binding protein 1
binder
Humans
URetinoic acid receptor responder protein 1
agonist
Humans
URetinal dehydrogenase 1
substrate
Humans
URetinal dehydrogenase 2
substrate
Humans
URetinoic acid-induced protein 3
regulator
Humans
ULipocalin-1
binder
Humans
UOdorant-binding protein 2a
binder
Humans
URetinol-binding protein 4
binder
Humans
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial
upregulator
Humans
UCarcinoembryonic antigen
downregulator
Humans
Absorption

Tretinoin applied topically is expected to remain on the stratum corneum and undergo minimal systemic absorption.4,7 In one study, the topical application of radiolabelled tretinoin for 28 days was associated with a total percutaneous absorption of 2%.4

The extent of absorption was examined after a once-daily application of 1.9 g of the combination product with benzoyl peroxide for 14 days. On Day 14, at steady-state, the mean Cmax was 0.15-0.19 ng/mL for tretinoin, 0.27-0.34 ng/mL for the metabolite 4-keto 13-cis retinoic acid, and 0.13-0.28 ng/mL for 13-cis retinoic acid, respectively. The Cmax varied across different age groups (children, adolescents, and adults). The corresponding ranges for the mean AUC0-24 were 0.63-2.06, 2.39-2.89, and 0.96-1.99 ng*h/mL.12

Following oral administration, the absolute bioavailability of tretinoin was approximately 50%.13 While the effect of food on tretinoin is unclear, food increases the oral absorption of retinoids, as a class.13,18 When the oral dose of 22.5 mg/m2 tretinoin was administered twice daily, the mean ± SD Cmax was 394 ± 89 ng/mL after the first dose and 138 ± 139 ng/mL after one week of continuous treatment. The area under the curve (AUC) was 537 ± 191 ng·h/mL after the first dose and 249 ± 185 ng·h/mL after one week of continuous treatment. The Tmax was between one and two hours.13

Volume of distribution

Tretinoin is rapidly and extensively distributed to tissues following oral administration but does not cross the blood-brain barrier. The apparent volume of distribution (Vd) of intravenous tretinoin is dose-dependent and significantly greater at low doses. The Vd was 0.52 ± 0.12 L/kg after 0.0125 mg/kg and 0.21 ± 0.05 L/kg after 0.25 mg/kg.5

Protein binding

Protein binding of tretinoin is greater than 95%, predominately to albumin.5,13 Plasma protein binding remains constant over the 10 to 500 ng/mL concentration range.13

Metabolism

Tretinoin is rapidly metabolized to form various oxidized and conjugated metabolites. It forms several metabolites stereoisomerization derivatives (9-cis-retinoic acid or alitretinoin and 13-cis-retinoic acid or isotretinoin), oxidation derivatives (4-hydroxy-retinoic acid, 4-oxo-retinoic acid, 18-hydroxy-retinoic acid, 5,6-epoxy-retinoic acid, 3,4-didehydro-retinoic acid and retinotaurine), stereoisomerization and oxidation derivatives (13-cis-4-oxo-retinoic acid), glucuronidation derivatives (retinoyl beta-glucuronide, 13-cis-retinoyl beta-glucuronide, 4-oxo-retinoyl beta-glucuronide, 5,6-epoxyretinoyl beta-glucuronide and 13-cis-4-oxo-retinoyl beta-glucuronide), nonpolar metabolites of retinoic acid, and retinoic acid esters.5

Tretinoin is metabolized by several CYP enzymes, including CYP3A4, CYP2C8, and CYP2E. It also undergoes glucuronidation by UGT2B7. The metabolites 4-oxo retinoic acid and 4-oxo trans retinoic acid glucuronide have one-third of the pharmacological activity of the parent compound.8,13 When the plasma concentrations decreased to one-third of their day-one concentrations after one week of continuous therapy, tretinoin induced its own metabolism.5,13

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Route of elimination

Tretinoin metabolites are excreted in bile and urine.18 Following administration of radiolabeled tretinoin at doses of 2.75 mg and 50 mg - which are 0.53 to 9.6 times the approved recommended dosage based on 1.7 m2, respectively - approximately 63% of the radioactivity was recovered in the urine within 72 hours, and 31% appeared in the feces within six days.13

Half-life

The terminal elimination half-life of tretinoin following initial dosing is 0.5 to 2 hours in patients with APL.13

Clearance

No information is available.

Adverse Effects
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Toxicity

The oral LD50 in rats is 2000 mg/kg. The dermal LD50 in rabbits is >2500 mg/kg.17

Reversible signs of hypervitaminosis A, such as headache, nausea, vomiting, and mucocutaneous symptoms, are expected to appear in tretinoin overdose. Overdosage with other retinoids has been associated with transient headache, facial flushing, cheilosis, abdominal pain, dizziness and ataxia: these symptoms have quickly resolved without apparent residual effects. here is no specific treatment in the case of an overdose and it is advised to treat patients experiencing tretinoin overdose in a special hematological unit.13

Pathways
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Tretinoin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Tretinoin can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Tretinoin can be decreased when combined with Acalabrutinib.
AcebutololTretinoin may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of elevated intracranial pressure can be increased when Aceclofenac is combined with Tretinoin.
Food Interactions
  • Take with food. Effect of food on tretinoin absorption is unclear, but food increases the bioavailability of retinoids drug class.

Products

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Product Images
International/Other Brands
Aberel (Janssen) / Aberela (Janssen) / Airol (Pierre Fabre Dermo) / Dermairol (Roche) / Eudyna (Zydus) / Kétrel (Bailleul) / Sotret (Ranbaxy Laboratories Inc.) / Stieva-A (Stiefel) / Vitinoin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AltrenoLotion0.5 mg/1gTopicalBausch Health US, LLC2018-08-24Not applicableUS flag
AltrenoLotion0.05 % w/wTopicalBausch Health, Canada Inc.Not applicableNot applicableCanada flag
AtralinGel0.05 g/100gTopicalBausch Health US, LLC2007-07-26Not applicableUS flag
AvitaCream0.25 mg/1gTopicalMylan Bertek Pharmaceuticals2015-11-012015-11-19US flag
AvitaGel0.25 mg/1gTopicalMylan Pharmaceuticals Inc.1998-03-182023-05-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Jamp TretinoinCapsule10 mgOralJamp Pharma Corporation2022-08-29Not applicableCanada flag
ObagiCream1 mg/1gTopicalYS PLUS CORPORATION2014-10-012015-12-31US flag
ObagiCream0.5 mg/1gTopicalYS PLUS CORPORATION2014-10-012015-12-31US flag
RefissaCream0.5 mg/1gTopicalCoria Laboratories2011-02-012016-05-01US flag
RefissaCream0.5 mg/1gTopicalSuneva Medical, Inc.2009-06-17Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ทีนา - เอ ครีมCream0.05 %w/wTopicalบริษัท 2 เอ็ม.(เมด-เมเกอร์) จำกัด จำกัด1990-01-30Not applicableThailand flag
เรติน - เอCream0.025 %w/wTopicalบริษัท โอลิค (ประเทศไทย) จำกัด1990-10-05Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACNATACTretinoin (0.025 %) + Clindamycin (1 %)GelTopicalFarmed S.R.L.2023-12-28Not applicableItaly flag
Acnatac 10 mg/g + 0,25 mg/g GelTretinoin (0.25 mg/g) + Clindamycin (10 mg/g)GelTopicalMylan österreich Gmb H2013-03-26Not applicableAustria flag
AKNEMYCIN PLUS SOLUTIONTretinoin (0.025 g/100g) + Erythromycin (4 g/100g)SolutionTopicalZUELLIG PHARMA PTE. LTD.2000-02-04Not applicableSingapore flag
ALBAVANCE FTretinoin (0.01 %) + Fluocinolone acetonide (4 %) + Hydroquinone (0.05 %)CreamImmortal Pharmaceutical Laboratories2017-09-182027-04-19Indonesia flag
BALISA VASTretinoin (0.3 mg/g) + Urea (120 mg/g)CreamTopical2006-04-01Not applicableGermany flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
011010 Niacinamide 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011013 Niacinamide 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011020 Niacinamide 4% / Tretinoin 0.05%Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011021 Niacinamide 4% / Tretinoin 0.05%Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag

Categories

ATC Codes
L01XF01 — TretinoinD10AD51 — Tretinoin, combinationsD10AD01 — Tretinoin
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5688UTC01R
CAS number
302-79-4
InChI Key
SHGAZHPCJJPHSC-YCNIQYBTSA-N
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

References

General References
  1. Yoham AL, Casadesus D: Tretinoin. . [Article]
  2. Kang S: The mechanism of action of topical retinoids. Cutis. 2005 Feb;75(2 Suppl):10-3; discussion 13. [Article]
  3. Baldwin HE, Nighland M, Kendall C, Mays DA, Grossman R, Newburger J: 40 years of topical tretinoin use in review. J Drugs Dermatol. 2013 Jun 1;12(6):638-42. [Article]
  4. Thorne EG: Long-term clinical experience with a topical retinoid. Br J Dermatol. 1992 Sep;127 Suppl 41:31-6. doi: 10.1111/j.1365-2133.1992.tb16985.x. [Article]
  5. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
  6. Gillis JC, Goa KL: Tretinoin. A review of its pharmacodynamic and pharmacokinetic properties and use in the management of acute promyelocytic leukaemia. Drugs. 1995 Nov;50(5):897-923. doi: 10.2165/00003495-199550050-00008. [Article]
  7. Noble S, Wagstaff AJ: Tretinoin. A review of its pharmacological properties and clinical efficacy in the topical treatment of photodamaged skin. Drugs Aging. 1995 Jun;6(6):479-96. doi: 10.2165/00002512-199506060-00008. [Article]
  8. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  9. Marill J, Idres N, Capron CC, Nguyen E, Chabot GG: Retinoic acid metabolism and mechanism of action: a review. Curr Drug Metab. 2003 Feb;4(1):1-10. doi: 10.2174/1389200033336900. [Article]
  10. Sitohang IBS, Makes WI, Sandora N, Suryanegara J: Topical tretinoin for treating photoaging: A systematic review of randomized controlled trials. Int J Womens Dermatol. 2022 Mar 25;8(1):e003. doi: 10.1097/JW9.0000000000000003. eCollection 2022 Mar. [Article]
  11. Mukherjee S, Date A, Patravale V, Korting HC, Roeder A, Weindl G: Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety. Clin Interv Aging. 2006;1(4):327-48. doi: 10.2147/ciia.2006.1.4.327. [Article]
  12. DailyMed Label: TWYNEO (tretinoin and benzoyl peroxide) topical cream [Link]
  13. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
  14. DailyMed Label: CLINDAMYCIN PHOSPHATE and TRETINOIN Gel 1.2% / 0.025%, for topical use only [Link]
  15. DailyMed Label: Tretinoin Topical Cream or Gel [Link]
  16. DailyMed Label: TRIDERMA (hydroquinone, tretinoin, fluocinolone acetonide) topical cream [Link]
  17. Medisca: TRETINOIN, USP (Retinoic Acid) MSDS [Link]
  18. Cancer Care Ontario Tretinoin Monograph [Link]
Human Metabolome Database
HMDB0001852
KEGG Drug
D00094
KEGG Compound
C00777
PubChem Compound
5538
PubChem Substance
46504843
ChemSpider
392618
BindingDB
31883
RxNav
10753
ChEBI
15367
ChEMBL
CHEMBL38
ZINC
ZINC000012358651
Therapeutic Targets Database
DNC000117
PharmGKB
PA164746900
PDBe Ligand
REA
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tretinoin
PDB Entries
1cbr / 1cbs / 1fem / 1g5y / 1gx9 / 1n4h / 1rlb / 2acl / 2fr3 / 2g78
show 12 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentPhotodamaged Skin / Solar Elastosis1
4CompletedOtherAcne / Healthy Volunteers (HV)1
4CompletedPreventionAcne1
4CompletedTreatmentAcne2
4CompletedTreatmentAcne Vulgaris9

Pharmacoeconomics

Manufacturers
  • Hoffmann la roche inc
  • Genpharm inc
  • Barr laboratories inc
  • Ranbaxy pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Mylan bertek pharmaceuticals inc
  • Ortho dermatologics
  • Johnson and johnson consumer companies inc
  • Spear pharmaceuticals inc
  • Triax pharmaceuticals llc
  • Dow pharmaceutical sciences inc
  • Mylan pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Wockhardt eu operations (swiss) ag
  • Ranbaxy Pharmaceuticals Inc.
Packagers
  • Actavis Group
  • Ameri-Pac Inc.
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Cardinal Health
  • Catalent Pharma Solutions
  • Contract Pharm
  • Coria Laboratories
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DPT Laboratories Ltd.
  • Draxis Specialty Pharmaceuticals Inc.
  • F Hoffmann-La Roche Ltd.
  • Galderma Laboratories
  • Genesis Pharmaceutical Inc.
  • Hill Laboratories Inc.
  • Medicis Pharmaceutical Co.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Obagi Medical Products Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmedix
  • Physicians Total Care Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Rouses Point Pharmaceuticals LLC
  • Sandoz
  • Spear Dermatology Products Inc.
  • Stiefel Labs
  • Triax Pharmaceuticals LLC
  • Valeant Ltd.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
LotionTopical50 mg
SolutionTopical0.05 g
GelTopical0.025 %
CreamTopical0.04 g
CreamTopical0.1 %
CapsuleOral10.000 mg
CreamTopical0.5 MG/G
SolutionTopical0.5 MG/ML
SolutionTopical4 g/100g
GelTopical0.05 g
LotionTopical0.05 % w/w
LotionTopical0.5 mg/1g
CapsuleOral10.0000 mg
SolutionTopical0.025 g
GelTopical0.025 g
LotionTopical
LotionTopical0.05 g
KitTopical
CreamTopical
EmulsionTopical
Cream
CreamTopical0.05 g/100g
CreamTopical0.2 mg/1g
CreamTopical0.05 g
CreamTopical0.025 g
LotionTopical
CreamTopical0.1 mg/1g
GelTopical0.01 % w/w
GelTopical0.0100 g
GelTopical0.025 % w/w
LiquidTopical0.5 mg/1mL
GelCutaneous
GelTopical0.04 % w/w
GelTopical0.1 % w/w
GelTopical0.4 mg/1g
GelTopical0.6 mg/1g
GelTopical1 mL/1g
GelTopical400 mL/1g
CreamTopical0.01 %
CreamTopical0.050 g
GelTopical
SolutionTopical
LiquidTopical.05 %
CreamTopical0.01 % w/w
CreamTopical0.025 % w/w
CreamTopical0.05 % w/w
CreamTopical0.1 % w/w
SolutionTopical0.025 %
GelTopical.01 %
CreamTopical0.1 g
CreamCutaneous0.050 g
CreamTopical
CreamTopical0.375 mg/1g
GelTopical0.1 mg/1g
GelTopical0.25 mg/1g
CreamTopical0.75 mg/1g
CapsuleOral10 mg/1
CreamTopical0.025 mg/1g
CreamTopical0.05 mg/1g
CreamTopical0.25 mg/1g
CreamTopical0.5 mg/1g
CreamTopical1 mg/1g
CreamTopical1.0 mg/1g
GelTopical0.01 mg/1g
GelTopical0.025 mg/1g
GelTopical0.04 mg/1g
GelTopical0.05 g/100g
GelTopical0.5 mg/1g
GelTopical0.8 mg/1g
PowderNot applicable1 g/1g
GelTopical1 mg/1g
Cream; kit; lotionTopical
KitTopical0.25 mg/1g
KitTopical0.5 mg/1g
KitTopical1 mg/1g
CreamCutaneous
CreamTopical0.1 mg/g
GelTopical
CapsuleOral10 mg
Capsule, liquid filledOral10 mg/1
Capsule, gelatin coatedOral
CapsuleOral
Capsule, liquid filledOral10 mg
CreamTopical0.025 %
CreamTopical0.05 %
GelTopical0.025 %
SolutionTopical
GelTopical0.01 %
GelTopical0.05 %
CreamTopical.025 %
CreamTopical.05 %
CreamTopical.1 %
GelTopical.025 %
GelTopical0.1 %w/w
GelTopical0.05 %w/w
CreamTopical0.025 %w/w
CreamTopical0.05 %w/w
Prices
Unit descriptionCostUnit
Tretinoin (Emollient) 0.05% Cream 60 gm Tube200.07USD tube
Tri-Luma 0.01-4-0.05% Cream 30 gm Tube199.99USD tube
Solage 2-0.01% Solution 30ml Bottle168.67USD bottle
Tretinoin (Emollient) 0.05% Cream 40 gm Tube135.99USD tube
Tretinoin 0.1% Cream 45 gm Tube114.16USD tube
Tretinoin 0.025% Gel 45 gm Tube99.64USD tube
Tretinoin 0.01% Gel 45 gm Tube98.85USD tube
Tretinoin 0.05% Cream 45 gm Tube97.94USD tube
Tretinoin 0.025% Cream 45 gm Tube83.97USD tube
Tretinoin acid powder74.21USD g
Tretinoin 0.1% Cream 20 gm Tube60.96USD tube
Tretinoin 0.05% Cream 20 gm Tube52.23USD tube
Tretinoin 0.025% Cream 20 gm Tube44.36USD tube
Tretinoin 0.025% Gel 15 gm Tube42.26USD tube
Tretinoin 0.01% Gel 15 gm Tube35.99USD tube
Vesanoid 10 mg capsule30.32USD capsule
Accutane 40 mg capsule27.62USD capsule
Tretinoin 10 mg capsule27.29USD capsule
Accutane 20 mg capsule23.77USD capsule
Amnesteem 40 mg capsule22.6USD capsule
Claravis 40 mg capsule21.73USD capsule
Accutane 10 mg capsule20.05USD capsule
Amnesteem 20 mg capsule19.45USD capsule
Claravis 20 mg capsule18.7USD capsule
Claravis 30 mg capsule16.78USD capsule
Amnesteem 10 mg capsule16.4USD capsule
Claravis 10 mg capsule15.77USD capsule
Sotret 40 mg capsule10.08USD capsule
Sotret 20 mg capsule8.67USD capsule
Sotret 30 mg capsule8.44USD capsule
Sotret 10 mg capsule7.31USD capsule
Tri-luma cream6.4USD g
Retin-a micro 0.04% gel5.65USD g
Retin-a micro 0.1% gel5.65USD g
Solage topical solution5.59USD ml
Retin-a micro pump 0.04% gel4.74USD g
Retin-a micro pump 0.1% gel4.74USD g
Retin-a 0.05% cream4.64USD g
Retin-a 0.1% cream4.51USD g
Renova 0.02% cream4.46USD g
Renova pump 0.02% cream4.28USD g
Retin-a 0.025% cream4.14USD g
Refissa 0.05% cream3.6USD g
Tretinoin 0.05% emollient crm3.38USD g
Avita 0.025% cream3.19USD g
Tretinoin 0.1% cream2.36USD g
Tretinoin 0.025% cream2.17USD g
Tretinoin 0.05% cream2.02USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5470567No1995-11-282010-03-19US flag
US5955109No1999-09-212016-09-21US flag
US6353029No2002-03-052020-08-24US flag
US6531141No2003-03-112020-03-07US flag
US8247395No2012-08-212022-10-22US flag
US8653053No2014-02-182022-10-25US flag
US7939516No2011-05-102025-05-04US flag
US7915243No2011-03-292026-03-22US flag
US6387383No2002-05-142020-08-03US flag
US6517847No2003-02-112020-08-03US flag
US10653656No2020-05-192038-08-22US flag
US9868103No2018-01-162028-08-08US flag
US11071878No2021-07-272030-12-30US flag
US10420743No2019-09-242038-07-12US flag
US10653899No2020-05-192030-12-30US flag
US8617580No2013-12-312028-02-03US flag
US11324710No2018-08-222038-08-22US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178-184https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf
logP6.3https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.00477 mg/mLALOGPS
logP5.66ALOGPS
logP5.01Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.76Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity97.79 m3·mol-1Chemaxon
Polarizability36.85 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9311
Caco-2 permeable+0.7603
P-glycoprotein substrateNon-substrate0.6144
P-glycoprotein inhibitor INon-inhibitor0.8912
P-glycoprotein inhibitor IINon-inhibitor0.8088
Renal organic cation transporterNon-inhibitor0.8639
CYP450 2C9 substrateNon-substrate0.8221
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6025
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8831
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9301
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9252
Ames testNon AMES toxic0.8944
CarcinogenicityNon-carcinogens0.7081
BiodegradationReady biodegradable0.5554
Rat acute toxicity2.1455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9562
hERG inhibition (predictor II)Non-inhibitor0.9538
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0390000000-af1a6974c2a7872f36c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-82a486e1feafa5cf4f1b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lu-2970000000-05e8c3f4df3fed93b093
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-08192331c8e265ce508b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2890000000-2b136364b4a3a972b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-4910000000-f6c3b4ffdf3dc3f695a2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0390000000-af1a6974c2a7872f36c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-82a486e1feafa5cf4f1b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lu-2970000000-05e8c3f4df3fed93b093
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-08192331c8e265ce508b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2890000000-2b136364b4a3a972b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-4910000000-f6c3b4ffdf3dc3f695a2
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-202.3292981
predicted
DarkChem Lite v0.1.0
[M-H]-204.5572981
predicted
DarkChem Lite v0.1.0
[M-H]-192.63275
predicted
DeepCCS 1.0 (2019)
[M-H]-202.3292981
predicted
DarkChem Lite v0.1.0
[M-H]-204.5572981
predicted
DarkChem Lite v0.1.0
[M-H]-202.3292981
predicted
DarkChem Lite v0.1.0
[M-H]-204.5572981
predicted
DarkChem Lite v0.1.0
[M-H]-192.63275
predicted
DeepCCS 1.0 (2019)
[M-H]-192.63275
predicted
DeepCCS 1.0 (2019)
[M+H]+194.99077
predicted
DeepCCS 1.0 (2019)
[M+H]+194.99077
predicted
DeepCCS 1.0 (2019)
[M+H]+194.99077
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.33412
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.33412
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.33412
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARA
Uniprot ID
P10276
Uniprot Name
Retinoic acid receptor alpha
Molecular Weight
50770.805 Da
References
  1. Vollberg TM Sr, Nervi C, George MD, Fujimoto W, Krust A, Jetten AM: Retinoic acid receptors as regulators of human epidermal keratinocyte differentiation. Mol Endocrinol. 1992 May;6(5):667-76. [Article]
  2. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARB
Uniprot ID
P10826
Uniprot Name
Retinoic acid receptor beta
Molecular Weight
50488.63 Da
References
  1. Steidl U, Schroeder T, Steidl C, Kobbe G, Graef T, Bork S, Pechtel S, Kliszewski S, Kuendgen A, Rohr UP, Fenk R, Schroeder M, Haase D, Haas R, Kronenwett R: Distinct gene expression pattern of malignant hematopoietic stem and progenitor cells in polycythemia vera. Ann N Y Acad Sci. 2005 Jun;1044:94-108. [Article]
  2. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARG
Uniprot ID
P13631
Uniprot Name
Retinoic acid receptor gamma
Molecular Weight
50341.405 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Reddy AP, Chen JY, Zacharewski T, Gronemeyer H, Voorhees JJ, Fisher GJ: Characterization and purification of human retinoic acid receptor-gamma 1 overexpressed in the baculovirus-insect cell system. Biochem J. 1992 Nov 1;287 ( Pt 3):833-40. [Article]
  4. Kamei Y, Kawada T, Kazuki R, Sugimoto E: Retinoic acid receptor gamma 2 gene expression is up-regulated by retinoic acid in 3T3-L1 preadipocytes. Biochem J. 1993 Aug 1;293 ( Pt 3):807-12. [Article]
  5. Borger DR, Mi Y, Geslani G, Zyzak LL, Batova A, Engin TS, Pirisi L, Creek KE: Retinoic acid resistance at late stages of human papillomavirus type 16-mediated transformation of human keratinocytes arises despite intact retinoid signaling and is due to a loss of sensitivity to transforming growth factor-beta. Virology. 2000 May 10;270(2):397-407. [Article]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  8. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Curator comments
Tretinoin interacts 40-fold less efficiently with RXR-alpha than with RAR-alpha.
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 Da
References
  1. Mizuguchi Y, Wada A, Nakagawa K, Ito M, Okano T: Antitumoral activity of 13-demethyl or 13-substituted analogues of all-trans retinoic acid and 9-cis retinoic acid in the human myeloid leukemia cell line HL-60. Biol Pharm Bull. 2006 Sep;29(9):1803-9. [Article]
  2. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRB
Uniprot ID
P28702
Uniprot Name
Retinoic acid receptor RXR-beta
Molecular Weight
56921.38 Da
References
  1. Stafslien DK, Vedvik KL, De Rosier T, Ozers MS: Analysis of ligand-dependent recruitment of coactivator peptides to RXRbeta in a time-resolved fluorescence resonance energy transfer assay. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):82-9. Epub 2006 Dec 20. [Article]
  2. Redfern CP: Enhancing enhancers: new complexities in the retinoid regulation of gene expression. Biochem J. 2004 Oct 1;383(Pt 1):e1-2. [Article]
  3. Nagasawa H, Takahashi S, Kobayashi A, Tazawa H, Tashima Y, Sato K: Effect of retinoic acid on murine preosteoblastic MC3T3-E1 cells. J Nutr Sci Vitaminol (Tokyo). 2005 Oct;51(5):311-8. [Article]
  4. Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
  5. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
  6. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRG
Uniprot ID
P48443
Uniprot Name
Retinoic acid receptor RXR-gamma
Molecular Weight
50870.72 Da
References
  1. Koda T, Imai H, Morita M: Antiestrogenic activity of vitamin A in in vivo uterotrophic assay. Life Sci. 2007 Feb 13;80(10):945-9. Epub 2006 Nov 22. [Article]
  2. He JC, Lu TC, Fleet M, Sunamoto M, Husain M, Fang W, Neves S, Chen Y, Shankland S, Iyengar R, Klotman PE: Retinoic acid inhibits HIV-1-induced podocyte proliferation through the cAMP pathway. J Am Soc Nephrol. 2007 Jan;18(1):93-102. Epub 2006 Dec 20. [Article]
  3. Day RM, Lee YH, Park AM, Suzuki YJ: Retinoic acid inhibits airway smooth muscle cell migration. Am J Respir Cell Mol Biol. 2006 Jun;34(6):695-703. Epub 2006 Feb 2. [Article]
  4. Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
  5. Wang J, Yen A: A novel retinoic acid-responsive element regulates retinoic acid-induced BLR1 expression. Mol Cell Biol. 2004 Mar;24(6):2423-43. [Article]
  6. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name
CRABP1
Uniprot ID
P29762
Uniprot Name
Cellular retinoic acid-binding protein 1
Molecular Weight
15565.45 Da
References
  1. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Not Available
Specific Function
Inhibitor of the cytoplasmic carboxypeptidase AGBL2, may regulate the alpha-tubulin tyrosination cycle.
Gene Name
RARRES1
Uniprot ID
P49788
Uniprot Name
Retinoic acid receptor responder protein 1
Molecular Weight
33284.865 Da
References
  1. Youssef EM, Chen XQ, Higuchi E, Kondo Y, Garcia-Manero G, Lotan R, Issa JP: Hypermethylation and silencing of the putative tumor suppressor Tazarotene-induced gene 1 in human cancers. Cancer Res. 2004 Apr 1;64(7):2411-7. [Article]
  2. Zirn B, Samans B, Spangenberg C, Graf N, Eilers M, Gessler M: All-trans retinoic acid treatment of Wilms tumor cells reverses expression of genes associated with high risk and relapse in vivo. Oncogene. 2005 Aug 4;24(33):5246-51. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name
ALDH1A1
Uniprot ID
P00352
Uniprot Name
Retinal dehydrogenase 1
Molecular Weight
54861.44 Da
References
  1. Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
  2. Everts HB, King LE Jr, Sundberg JP, Ong DE: Hair cycle-specific immunolocalization of retinoic acid synthesizing enzymes Aldh1a2 and Aldh1a3 indicate complex regulation. J Invest Dermatol. 2004 Aug;123(2):258-63. [Article]
  3. Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [Article]
  4. Matt N, Dupe V, Garnier JM, Dennefeld C, Chambon P, Mark M, Ghyselinck NB: Retinoic acid-dependent eye morphogenesis is orchestrated by neural crest cells. Development. 2005 Nov;132(21):4789-800. Epub 2005 Oct 5. [Article]
  5. Kim H, Lapointe J, Kaygusuz G, Ong DE, Li C, van de Rijn M, Brooks JD, Pollack JR: The retinoic acid synthesis gene ALDH1a2 is a candidate tumor suppressor in prostate cancer. Cancer Res. 2005 Sep 15;65(18):8118-24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal...
Gene Name
ALDH1A2
Uniprot ID
O94788
Uniprot Name
Retinal dehydrogenase 2
Molecular Weight
56723.495 Da
References
  1. Mic FA, Sirbu IO, Duester G: Retinoic acid synthesis controlled by Raldh2 is required early for limb bud initiation and then later as a proximodistal signal during apical ectodermal ridge formation. J Biol Chem. 2004 Jun 18;279(25):26698-706. Epub 2004 Apr 6. [Article]
  2. Bordelon T, Montegudo SK, Pakhomova S, Oldham ML, Newcomer ME: A disorder to order transition accompanies catalysis in retinaldehyde dehydrogenase type II. J Biol Chem. 2004 Oct 8;279(41):43085-91. Epub 2004 Aug 7. [Article]
  3. Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
  4. Doxakis E, Davies AM: Retinoic acid negatively regulates GDNF and neurturin receptor expression and responsiveness in embryonic chicken sympathetic neurons. Mol Cell Neurosci. 2005 Aug;29(4):617-27. [Article]
  5. Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
G-protein coupled receptor activity
Specific Function
Orphan receptor. Could be involved in modulating differentiation and maintaining homeostasis of epithelial cells. This retinoic acid-inducible GPCR provide evidence for a possible interaction betwe...
Gene Name
GPRC5A
Uniprot ID
Q8NFJ5
Uniprot Name
Retinoic acid-induced protein 3
Molecular Weight
40250.69 Da
References
  1. Xu J, Tian J, Shapiro SD: Normal lung development in RAIG1-deficient mice despite unique lung epithelium-specific expression. Am J Respir Cell Mol Biol. 2005 May;32(5):381-7. Epub 2005 Jan 27. [Article]
  2. Inoue S, Nambu T, Shimomura T: The RAIG family member, GPRC5D, is associated with hard-keratinized structures. J Invest Dermatol. 2004 Mar;122(3):565-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Cysteine-type endopeptidase inhibitor activity
Specific Function
Could play a role in taste reception. Could be necessary for the concentration and delivery of sapid molecules in the gustatory system. Can bind various ligands, with chemical structures ranging fr...
Gene Name
LCN1
Uniprot ID
P31025
Uniprot Name
Lipocalin-1
Molecular Weight
19249.845 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Odorant binding
Specific Function
Probably binds and transports small hydrophobic volatile molecules with a higher affinity for aldehydes and large fatty acids.
Gene Name
OBP2A
Uniprot ID
Q9NY56
Uniprot Name
Odorant-binding protein 2a
Molecular Weight
19318.245 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Retinol transporter activity
Specific Function
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name
RBP4
Uniprot ID
P02753
Uniprot Name
Retinol-binding protein 4
Molecular Weight
23009.8 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Upregulator
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific Function
Kinase that plays a key role in regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvate de...
Gene Name
PDK4
Uniprot ID
Q16654
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial
Molecular Weight
46468.79 Da
References
  1. Kwon HS, Huang B, Ho Jeoung N, Wu P, Steussy CN, Harris RA: Retinoic acids and trichostatin A (TSA), a histone deacetylase inhibitor, induce human pyruvate dehydrogenase kinase 4 (PDK4) gene expression. Biochim Biophys Acta. 2006 Mar-Apr;1759(3-4):141-51. Epub 2006 Apr 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Not Available
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q14081
Uniprot Name
Carcinoembryonic antigen
Molecular Weight
4903.595 Da
References
  1. Friedman J, Seger M, Levinsky H, Allalouf D: Modulation of carcinoembryonic antigen release by HT-29 colon carcinoma line in the presence of different agents. Experientia. 1987 Oct 15;43(10):1121-2. doi: 10.1007/BF01956058. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  3. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Leukotriene-b4 20-monooxygenase activity
Specific Function
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
Gene Name
CYP4A11
Uniprot ID
Q02928
Uniprot Name
Cytochrome P450 4A11
Molecular Weight
59347.31 Da
References
  1. Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
Gene Name
CYP26A1
Uniprot ID
O43174
Uniprot Name
Cytochrome P450 26A1
Molecular Weight
56198.11 Da
References
  1. Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. doi: 10.1038/sj.jid.5700432. Epub 2006 Jun 15. [Article]
  2. Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80. doi: 10.1097/FPC.0b013e32801152d6. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Maiti TK, Ghosh KS, Debnath J, Dasgupta S: Binding of all-trans retinoic acid to human serum albumin: fluorescence, FT-IR and circular dichroism studies. Int J Biol Macromol. 2006 May 30;38(3-5):197-202. Epub 2006 Mar 6. [Article]
  2. N'soukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA: Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol. 2007 Apr 10;40(5):484-90. Epub 2006 Nov 24. [Article]
  3. Karnaukhova E: Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. Epub 2006 Dec 2. [Article]
  4. Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
  5. FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name
CRABP1
Uniprot ID
P29762
Uniprot Name
Cellular retinoic acid-binding protein 1
Molecular Weight
15565.45 Da
References
  1. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
  2. Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
  3. Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name
CRABP2
Uniprot ID
P29373
Uniprot Name
Cellular retinoic acid-binding protein 2
Molecular Weight
15692.925 Da
References
  1. Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
  2. Ohnishi K: PML-RARalpha inhibitors (ATRA, tamibaroten, arsenic troxide) for acute promyelocytic leukemia. Int J Clin Oncol. 2007 Oct;12(5):313-7. Epub 2007 Oct 22. [Article]
  3. Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
  4. Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48