Identification
NameIsotretinoin
Accession NumberDB00982  (APRD00140)
TypeSmall Molecule
GroupsApproved
Description

Isotretinoin is a medication used for the treatment of severe acne. It is sometimes used in prevention of certain skin cancers. It is a retinoid, meaning it derives from vitamin A and is found in small quantities naturally in the body. Isotretinoin binds to and activates nuclear retinoic acid receptors (RAR), thereby regulating cell proliferation and differentiation. This agent also exhibits immunomodulatory and anti-inflammatory responses and inhibits ornithine decarboxylase, thereby decreasing polyamine synthesis and keratinization.

Structure
Thumb
Synonyms
(7e,9e,11e,13Z)-Retinoic acid
13-cis-Retinoic acid
13-cis-Vitamin a acid
13-RA
cis-RA
Isotretinoina
Isotretinoine
Isotretinoino
Isotretinoinum
Neovitamin a acid
External IDs RO 4-3780 / RO-4-3780
Product Ingredients Not Available
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AbsoricaCapsule30 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
AbsoricaCapsule35 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
AbsoricaCapsule20 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
AbsoricaCapsule40 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
AbsoricaCapsule25 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
AbsoricaCapsule10 mg/1OralRanbaxy Inc.2012-06-08Not applicableUs
Accutane RocheCapsule10 mgOralHoffmann La Roche1983-12-31Not applicableCanada
Accutane RocheCapsule40 mgOralHoffmann La Roche1983-12-31Not applicableCanada
ClarusCapsule40 mgOralMylan Pharmaceuticals2005-04-01Not applicableCanada
ClarusCapsule10 mgOralMylan Pharmaceuticals2005-04-01Not applicableCanada
EpurisCapsule30 mgOralCipher Pharmaceuticals Inc.2013-05-07Not applicableCanada
EpurisCapsule10 mgOralCipher Pharmaceuticals Inc.2013-05-07Not applicableCanada
EpurisCapsule40 mgOralCipher Pharmaceuticals Inc.2013-05-07Not applicableCanada
EpurisCapsule20 mgOralCipher Pharmaceuticals Inc.2013-05-07Not applicableCanada
Isotrex Gel 0.05%Gel0.05 %TopicalStiefel Laboratories, Inc.1992-12-312005-05-03Canada
Ran-isotretinoinCapsule10 mgOralRanbaxy Inc.Not applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmnesteemCapsule40 mg/1OralMylan Pharmaceuticals2002-11-11Not applicableUs
AmnesteemCapsule10 mg/1OralPhysicians Total Care, Inc.2010-11-02Not applicableUs
AmnesteemCapsule20 mg/1OralMylan Pharmaceuticals2002-11-11Not applicableUs
AmnesteemCapsule20 mg/1OralPhysicians Total Care, Inc.2009-09-14Not applicableUs
AmnesteemCapsule40 mg/1OralPhysicians Total Care, Inc.2009-07-14Not applicableUs
AmnesteemCapsule10 mg/1OralMylan Pharmaceuticals2002-11-11Not applicableUs
ClaravisCapsule, liquid filled30 mg/1OralTeva2006-05-18Not applicableUs
ClaravisCapsule30 mg/1OralPhysicians Total Care, Inc.2013-10-04Not applicableUs00555 1056 86 nlmimage10 da306d53
ClaravisCapsule, liquid filled10 mg/1OralTeva2003-05-09Not applicableUs00555 1054 86 nlmimage10 d5306ae3
ClaravisCapsule, liquid filled40 mg/1OralTeva2003-05-09Not applicableUs
ClaravisCapsule20 mg/1OralPhysicians Total Care, Inc.2011-09-14Not applicableUs00555 1055 86 nlmimage10 e33071d3
ClaravisCapsule, liquid filled20 mg/1OralTeva2003-05-09Not applicableUs
ClaravisCapsule40 mg/1OralPhysicians Total Care, Inc.2011-09-20Not applicableUs00555 1057 86 nlmimage10 de306f63
MyorisanCapsule, liquid filled20 mg/1OralVersa Pharm Incorporated2012-05-01Not applicableUs
MyorisanCapsule, liquid filled40 mg/1OralPhysicians Total Care, Inc.2012-08-23Not applicableUs
MyorisanCapsule, liquid filled30 mg/1OralVersa Pharm Incorporated2015-08-26Not applicableUs
MyorisanCapsule, liquid filled20 mg/1OralPhysicians Total Care, Inc.2012-10-29Not applicableUs
MyorisanCapsule, liquid filled10 mg/1OralVersa Pharm Incorporated2012-05-01Not applicableUs
MyorisanCapsule, liquid filled40 mg/1OralVersa Pharm Incorporated2012-05-01Not applicableUs
ZenataneCapsule, gelatin coated20 mg/1OralPhysicians Total Care, Inc.2014-05-16Not applicableUs
ZenataneCapsule, gelatin coated20 mg/1OralDr Reddy's Laboratories2013-03-26Not applicableUs
ZenataneCapsule, gelatin coated10 mg/1OralDr Reddy's Laboratories2013-03-26Not applicableUs
ZenataneCapsule, gelatin coated40 mg/1OralPhysicians Total Care, Inc.2014-05-16Not applicableUs
ZenataneCapsule, gelatin coated40 mg/1OralDr Reddy's Laboratories2013-03-26Not applicableUs
ZenataneCapsule, gelatin coated30 mg/1OralDr Reddy's Laboratories2015-03-09Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AccutaneNot Available
AmnesteemNot Available
ClaravisNot Available
Brand mixturesNot Available
Categories
UNIIEH28UP18IF
CAS number4759-48-2
WeightAverage: 300.4351
Monoisotopic: 300.20893014
Chemical FormulaC20H28O2
InChI KeySHGAZHPCJJPHSC-XFYACQKRSA-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
(2Z,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
Pharmacology
Indication

For the treatment of severe recalcitrant nodular acne

Structured Indications
Pharmacodynamics

Isotretinoin, a retinoid, is indicated in the treatment of severe recalcitrant nodular acne. Nodules are inflammatory lesions with a diameter of 5 mm or greater. The nodules may become suppurative or hemorrhagic. "Severe," by definition, means "many" as opposed to "few or several" nodules. Clinical improvement in nodular acne patients occurs in association with a reduction in sebum secretion. The decrease in sebum secretion is temporary and is related to the dose and duration of treatment with Accutane, and reflects a reduction in sebaceous gland size and an inhibition of sebaceous gland differentiation.

Mechanism of action

Isotretinoin noticeably reduces the production of sebum and shrinks the sebaceous glands. It stabilises keratinization and prevents comedones from forming. It also reduces inflammation in moderate-severe inflammatory acne. The exact mechanism of action is unknown, however it is known that it alters DNA transcription.

TargetKindPharmacological actionActionsOrganismUniProt ID
Retinoic acid receptor alphaProteinunknown
other/unknown
HumanP10276 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding

99.9%

MetabolismNot Available
Route of elimination

Isotretinoin and its metabolites are further metabolized into conjugates, which are then excreted in urine and feces. The metabolites of isotretinoin and any conjugates are ultimately excreted in the feces and urine in relatively equal amounts (total of 65% to 83%).

Half life

17-50 hours

Clearance
  • 96 +/- 6.27 L/hr [severe recalcitrant nodular acne pediatric Patients, 12 to 15 Years]
Toxicity

Isotretinoin is teratogenic. It also causes mucocutaneous side effects suck as cheilitis, dry skin, and dry eyes.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
ChlorotrianiseneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Isotretinoin.Withdrawn
ChlortetracyclineThe risk or severity of adverse effects can be increased when Chlortetracycline is combined with Isotretinoin.Approved, Vet Approved
Conjugated estrogensThe therapeutic efficacy of Conjugated Equine Estrogens can be decreased when used in combination with Isotretinoin.Approved
DemeclocyclineThe risk or severity of adverse effects can be increased when Demeclocycline is combined with Isotretinoin.Approved
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Isotretinoin.Approved
DienestrolThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Isotretinoin.Approved
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Isotretinoin.Approved
DiethylstilbestrolThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Isotretinoin.Approved
DoxycyclineThe risk or severity of adverse effects can be increased when Doxycycline is combined with Isotretinoin.Approved, Investigational, Vet Approved
DrospirenoneThe therapeutic efficacy of Drospirenone can be decreased when used in combination with Isotretinoin.Approved
EstradiolThe therapeutic efficacy of Estradiol can be decreased when used in combination with Isotretinoin.Approved, Investigational, Vet Approved
EstramustineThe therapeutic efficacy of Estramustine can be decreased when used in combination with Isotretinoin.Approved
Estrogens, esterifiedThe therapeutic efficacy of Estrogens, esterified can be decreased when used in combination with Isotretinoin.Approved
Estrone sulfateThe therapeutic efficacy of Estrone sulfate can be decreased when used in combination with Isotretinoin.Approved
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Isotretinoin.Approved
Ethinyl EstradiolThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Isotretinoin.Approved
Ethynodiol diacetateThe therapeutic efficacy of Ethynodiol diacetate can be decreased when used in combination with Isotretinoin.Approved
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Isotretinoin.Approved, Investigational
GestodeneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Isotretinoin.Approved
HexestrolThe therapeutic efficacy of Hexestrol can be decreased when used in combination with Isotretinoin.Withdrawn
LevonorgestrelThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Isotretinoin.Approved, Investigational
LynestrenolThe therapeutic efficacy of Lynestrenol can be decreased when used in combination with Isotretinoin.Investigational
Medroxyprogesterone acetateThe therapeutic efficacy of Medroxyprogesterone acetate can be decreased when used in combination with Isotretinoin.Approved, Investigational
MestranolThe therapeutic efficacy of Mestranol can be decreased when used in combination with Isotretinoin.Approved
MethallenestrilThe therapeutic efficacy of Methallenestril can be decreased when used in combination with Isotretinoin.Experimental
MinocyclineThe risk or severity of adverse effects can be increased when Minocycline is combined with Isotretinoin.Approved, Investigational
MipomersenIsotretinoin may increase the hepatotoxic activities of Mipomersen.Approved
NorelgestrominThe therapeutic efficacy of Norelgestromin can be decreased when used in combination with Isotretinoin.Approved
NorgestimateThe therapeutic efficacy of Norgestimate can be decreased when used in combination with Isotretinoin.Approved
NorgestrelThe therapeutic efficacy of Norgestrel can be decreased when used in combination with Isotretinoin.Approved
OxytetracyclineThe risk or severity of adverse effects can be increased when Oxytetracycline is combined with Isotretinoin.Approved, Vet Approved
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Synthetic Conjugated Estrogens, A can be decreased when used in combination with Isotretinoin.Approved
TetracyclineThe risk or severity of adverse effects can be increased when Tetracycline is combined with Isotretinoin.Approved, Vet Approved
Vitamin AThe risk or severity of adverse effects can be increased when Vitamin A is combined with Isotretinoin.Approved, Nutraceutical, Vet Approved
Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water Do not take supplements containing Vitamin A.
  • Take with high-fat meal to increase absorption.
References
Synthesis Reference

Ashok Kumar, Dharmendra Singh, Ganesh Devidas Mahale, Ragnesh Kumar Rana, Mahesh Kharade, "PROCESS FOR PREPARATION OF HIGHLY PURE ISOTRETINOIN." U.S. Patent US20080207946, issued August 28, 2008.

US20080207946
General References
  1. Berard A, Azoulay L, Koren G, Blais L, Perreault S, Oraichi D: Isotretinoin, pregnancies, abortions and birth defects: a population-based perspective. Br J Clin Pharmacol. 2007 Feb;63(2):196-205. [PubMed:17214828 ]
  2. Holmes SC, Bankowska U, Mackie RM: The prescription of isotretinoin to women: is every precaution taken? Br J Dermatol. 1998 Mar;138(3):450-5. [PubMed:9580798 ]
  3. Amichai B, Shemer A, Grunwald MH: Low-dose isotretinoin in the treatment of acne vulgaris. J Am Acad Dermatol. 2006 Apr;54(4):644-6. [PubMed:16546586 ]
  4. Seukeran DC, Cunliffe WJ: Acne vulgaris in the elderly: the response to low-dose isotretinoin. Br J Dermatol. 1998 Jul;139(1):99-101. [PubMed:9764156 ]
  5. Tirado Sanchez A, Leon Dorantes G: [Erectile dysfunction during isotretinoin therapy]. Actas Urol Esp. 2005 Nov-Dec;29(10):974-6. [PubMed:16447596 ]
External Links
ATC CodesD10AD54 — Isotretinoin, combinationsD10AD04 — IsotretinoinD10BA01 — Isotretinoin
AHFS Codes
  • 84:92.00
PDB EntriesNot Available
FDA labelDownload (376 KB)
MSDSDownload (37.3 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAcute Myelogenous Leukaemia (AML) / Juvenile Myelomonocytic Leukemia / Myelodysplastic Syndrome1
1Active Not RecruitingTreatmentAdult Solid Neoplasm1
1CompletedNot AvailableSkin Infections (Acne)1
1CompletedTreatmentAcne1
1CompletedTreatmentAdult Grade III Lymphomatoid Granulomatosis / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Intraocular Lymphoma / Nodal marginal zone B-cell lymphomas / Primary Central Nervous System Non-Hodgkin Lymphoma / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Small Intestine Lymphoma / Splenic Marginal Zone Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Adult T-Cell Leukemia/Lymphoma / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma / Unspecified Adult Solid Tumor, Protocol Specific / Waldenstrom's Macroglobulinemia (WM)1
1CompletedTreatmentAnus Neoplasms / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentChildhood Acute Promyelocytic Leukemia (M3) / Childhood Atypical Teratoid/Rhabdoid Tumor / Childhood Burkitt Lymphoma / Childhood Chronic Myelogenous Leukemia / Childhood Diffuse Large Cell Lymphoma / Childhood Immunoblastic Large Cell Lymphoma / Juvenile Myelomonocytic Leukemia / Recurrent Childhood Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Recurrent Childhood Grade III Lymphomatoid Granulomatosis / Recurrent Childhood Large Cell Lymphoma / Recurrent Childhood Lymphoblastic Lymphoma / Recurrent Childhood Medulloblastoma / Recurrent Childhood Small Noncleaved Cell Lymphoma / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor / Recurrent Neuroblastoma / Recurrent/Refractory Childhood Hodgkin Lymphoma / Relapsing Chronic Myelogenous Leukemia / Unspecified Childhood Solid Tumor, Protocol Specific1
1CompletedTreatmentDisseminated Neuroblastoma / Recurrent Neuroblastoma / Regional Neuroblastoma1
1CompletedTreatmentEpidermolysis Bullosa1
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentLocalized Unresectable Neuroblastoma / Recurrent Neuroblastoma / Regional Neuroblastoma / Stage 4 Neuroblastoma / Stage 4S Neuroblastoma1
1CompletedTreatmentNeuroblastomas1
1SuspendedTreatmentRecurrent Neuroblastoma / Stage 4 Neuroblastoma1
1TerminatedTreatmentAdult Anaplastic Astrocytoma / Adult Anaplastic Oligodendroglioma / Adult Diffuse Astrocytoma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Adult Mixed Glioma / Adult Oligodendroglioma / Recurrent Adult Brain Tumor1
1TerminatedTreatmentNeuroblastomas1
1WithdrawnTreatmentNeuroblastomas1
1, 2Active Not RecruitingTreatmentAnaplastic Gliomas / Glioblastoma Multiforme1
1, 2CompletedTreatmentChronic Myeloproliferative Disorders / Leukemias / Myelodysplastic Syndromes / Thrombocytopenias1
1, 2CompletedTreatmentNeuroblastomas1
1, 2CompletedTreatmentRenal Cancers1
1, 2TerminatedTreatmentAlzheimer's Disease (AD)1
1, 2TerminatedTreatmentLeukemias1
1, 2TerminatedTreatmentRecurrent Renal Cell Cancer / Stage III Renal Cell Cancer / Stage IV Renal Cell Cancer1
1, 2Unknown StatusTreatmentNeuroblastomas1
2Active Not RecruitingTreatmentEffects of Immunotherapy / Neoplasm, Residual / Neuroblastomas1
2Active Not RecruitingTreatmentKlinefelter's Syndrome / Male Infertility / Y-chromosome Microdeletions1
2Active Not RecruitingTreatmentNeuroblastomas2
2CompletedPreventionActinic Keratosis (AK)1
2CompletedPreventionLung Cancers / Therapeutic Agent Toxicity1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentCervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Lung Cancers / Non-Melanomatous Skin Cancer / Penile Cancer1
2CompletedTreatmentEpidermal p53 Expression / Solar Elastosis1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedTreatmentJuvenile Myelomonocytic Leukemia1
2CompletedTreatmentLung Cancers1
2CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2CompletedTreatmentNeuroblastomas4
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentRecurrent Neuroblastoma1
2RecruitingTreatmentNeuroblastomas2
2RecruitingTreatmentNewly Diagnosed High Risk Neuroblastoma1
2TerminatedTreatmentCervical Cancers1
2TerminatedTreatmentMycosis Fungoides (MF) / Neoplasms, Hematologic / T-Cell Lymphomas1
2TerminatedTreatmentNeuroblastomas2
2TerminatedTreatmentPrimary Refractory Neuroblastoma1
2TerminatedTreatmentProstate Cancer1
2Unknown StatusTreatmentLeukemias1
2Unknown StatusTreatmentPhotodamage / Solar Elastosis1
3Active Not RecruitingTreatmentLocalized Resectable Neuroblastoma / Localized Unresectable Neuroblastoma / Recurrent Neuroblastoma / Regional Neuroblastoma / Stage 4 Neuroblastoma / Stage 4S Neuroblastoma1
3CompletedTreatmentAcne1
3CompletedTreatmentCervix, Dysplasia / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentDisseminated Neuroblastoma / Localized Resectable Neuroblastoma / Localized Unresectable Neuroblastoma / Regional Neuroblastoma / Stage 4 Neuroblastoma / Stage 4S Neuroblastoma1
3CompletedTreatmentHead and Neck Carcinoma1
3CompletedTreatmentLocalized Resectable Neuroblastoma / Localized Unresectable Neuroblastoma / Recurrent Neuroblastoma / Regional Neuroblastoma / Stage 4 Neuroblastoma / Stage 4S Neuroblastoma1
3CompletedTreatmentNeoplasms, Brain / Tumors, Central Nervous System1
3CompletedTreatmentNeuroblastomas2
3CompletedTreatmentPapular-pustular Rosacea1
3CompletedTreatmentRenal Cancers1
3CompletedTreatmentSevere Nodular Acne1
3Not Yet RecruitingTreatmentChildhood Ganglioneuroblastoma / Childhood Neuroblastoma / NMYC Gene Amplification / Recurrent Neuroblastoma1
3RecruitingTreatmentUntreated Childhood Medulloblastoma / Untreated Childhood Pineoblastoma / Untreated Childhood Supratentorial Primitive Neuroectodermal Tumor1
3Unknown StatusTreatmentNeuroblastomas2
3WithdrawnPreventionLung Cancers1
3WithdrawnTreatmentBrain and Central Nervous System Tumors1
4Active Not RecruitingTreatmentAcne1
4CompletedBasic ScienceAdverse Effects of Medical Drugs1
4CompletedTreatmentAcne Vulgaris1
4RecruitingBasic ScienceAcne Vulgaris1
4RecruitingOtherCYP2D6 Polymorphism1
4Unknown StatusPreventionVitreoretinopathy, Proliferative1
4Unknown StatusTreatmentDermatitis, Seborrheic / Quality of Life / Seborrhoeic dermatitis1
Not AvailableActive Not RecruitingTreatmentMedulloblastomas / Pinealoblastoma / Supratentorial Embryonal Tumor, Not Otherwise Specified / Untreated Childhood Medulloblastoma / Untreated Childhood Pineoblastoma / Untreated Childhood Supratentorial Primitive Neuroectodermal Tumor1
Not AvailableCompletedNot AvailableAcne1
Not AvailableCompletedPreventionMelanoma (Skin) / Non-Melanomatous Skin Cancer1
Not AvailableCompletedTreatmentDisseminated Neuroblastoma / Ganglioneuroblastoma / Localized Resectable Neuroblastoma / Localized Unresectable Neuroblastoma / Regional Neuroblastoma / Stage 4S Neuroblastoma1
Not AvailableRecruitingTreatmentNeuroblastomas3
Not AvailableRecruitingTreatmentToxic Epidermal Necrolysis1
Not AvailableUnknown StatusTreatmentNeuroblastomas1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral25 mg/1
CapsuleOral35 mg/1
CapsuleOral10 mg
CapsuleOral40 mg
CapsuleOral10 mg/1
CapsuleOral20 mg/1
CapsuleOral40 mg/1
CapsuleOral30 mg/1
CapsuleOral20 mg
CapsuleOral30 mg
GelTopical0.05 %
Capsule, liquid filledOral10 mg/1
Capsule, liquid filledOral20 mg/1
Capsule, liquid filledOral30 mg/1
Capsule, liquid filledOral40 mg/1
Capsule, gelatin coatedOral10 mg/1
Capsule, gelatin coatedOral20 mg/1
Capsule, gelatin coatedOral30 mg/1
Capsule, gelatin coatedOral40 mg/1
Prices
Unit descriptionCostUnit
Accutane 20 mg capsule23.77USD capsule
Amnesteem 40 mg capsule22.6USD capsule
Claravis 40 mg capsule22.6USD capsule
Amnesteem 20 mg capsule19.45USD capsule
Claravis 20 mg capsule18.7USD capsule
Claravis 30 mg capsule16.45USD capsule
Amnesteem 10 mg capsule16.4USD capsule
Claravis 10 mg capsule15.77USD capsule
Accutane 40 mg capsule14.88USD capsule
Accutane 10 mg capsule10.55USD 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
Clarus 40 mg Capsule2.14USD capsule
Clarus 10 mg Capsule1.05USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8367102 No2001-09-212021-09-21Us
US9089534 No2001-09-212021-09-21Us
US7435427 No2001-09-212021-09-21Us
US9078925 No2001-09-212021-09-21Us
US8952064 No2001-09-212021-09-21Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00477 mg/mLALOGPS
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m3·mol-1ChemAxon
Polarizability36.15 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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-12dbd83959268dee6dbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-4900000000-31c9262cbbf0bad5b738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fsl-9600000000-c6681587f0a9ae7a712eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative ParentsDiterpenoids / Medium-chain fatty acids / Methyl-branched fatty acids / Unsaturated fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsRetinoic acid / Diterpenoid / Retinoid skeleton / Medium-chain fatty acid / Branched fatty acid / Methyl-branched fatty acid / Fatty acyl / Unsaturated fatty acid / Fatty acid / Monocarboxylic acid or derivatives
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptorsretinoic acid (CHEBI:6067 ) / Retinoids (LMPR01090021 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
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 expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RX...
Gene Name:
RARA
Uniprot ID:
P10276
Uniprot Name:
Retinoic acid receptor alpha
Molecular Weight:
50770.805 Da
References
  1. Dahl AR, Grossi IM, Houchens DP, Scovell LJ, Placke ME, Imondi AR, Stoner GD, De Luca LM, Wang D, Mulshine JL: Inhaled isotretinoin (13-cis retinoic acid) is an effective lung cancer chemopreventive agent in A/J mice at low doses: a pilot study. Clin Cancer Res. 2000 Aug;6(8):3015-24. [PubMed:10955779 ]
  2. Zouboulis CC: Isotretinoin revisited: pluripotent effects on human sebaceous gland cells. J Invest Dermatol. 2006 Oct;126(10):2154-6. [PubMed:16983322 ]
  3. Vu-Dac N, Gervois P, Torra IP, Fruchart JC, Kosykh V, Kooistra T, Princen HM, Dallongeville J, Staels B: Retinoids increase human apo C-III expression at the transcriptional level via the retinoid X receptor. Contribution to the hypertriglyceridemic action of retinoids. J Clin Invest. 1998 Aug 1;102(3):625-32. [PubMed:9691099 ]
  4. Taylor LE, Bennett GD, Finnell RH: Altered gene expression in murine branchial arches following in utero exposure to retinoic acid. J Craniofac Genet Dev Biol. 1995 Jan-Mar;15(1):13-25. [PubMed:7601910 ]
  5. Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [PubMed:9204085 ]
Drug created on June 13, 2005 07:24 / Updated on September 01, 2017 10:34