Identification

Name
Tazarotene
Accession Number
DB00799  (APRD01246)
Type
Small Molecule
Groups
Approved, Investigational
Description

Tazarotene (marketed as Tazorac®, Avage® and Zorac®) is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). [Wikipedia]

Structure
Thumb
Synonyms
  • Tazarotene
  • Tazaroteno
  • Tazarotenum
External IDs
AGN 190168
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AvageCream1 mg/gCutaneousAllergan2003-01-07Not applicableUs
FabiorAerosol, foam1 mg/gTopicalStiefel Laboratories, Inc.2013-09-042018-09-30Us
FabiorAerosol, foam1 mg/gTopicalMayne Pharma Llc2017-03-10Not applicableUs
TazaroteneCream1 mg/gTopicalPacific Pharma2017-04-15Not applicableUs
TazaroteneCream.5 mg/gTopicalPacific Pharma2017-04-15Not applicableUs
TazoracGel1 mg/gOralPhysicians Total Care, Inc.2010-10-21Not applicableUs
TazoracGel1 mg/gCutaneousAllergan1997-08-01Not applicableUs
TazoracGel0.1 %TopicalAllergan1997-04-10Not applicableCanada
TazoracCream.5 mg/gCutaneousAllergan2000-11-15Not applicableUs
TazoracCream0.1 %TopicalAllergan2001-08-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TazaroteneCream1 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2017-04-03Not applicableUs
TazaroteneCream1 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2017-04-03Not applicableUs
International/Other Brands
Avage / Tazorac / Zorac
Categories
UNII
81BDR9Y8PS
CAS number
118292-40-3
Weight
Average: 351.462
Monoisotopic: 351.129299611
Chemical Formula
C21H21NO2S
InChI Key
OGQICQVSFDPSEI-UHFFFAOYSA-N
InChI
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
IUPAC Name
ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate
SMILES
CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1

Pharmacology

Indication

Used to treat psoriasis, acne and sun damaged skin (photodamage).

Structured Indications
Pharmacodynamics

Tazarotene is a prodrug and a member of the acetylenic class of retinoids. Following topical application, tazarotene undergoes esterase hydrolysis to form its active metabolite, tazarotenic acid. When treating acne tazarotene may be taken in conjunction with an oral antibiotic. Tazarotene has been shown in peer-reviewed double blinded studies to reduce: mottling and hyperpigmentation, sallowness, fine wrinkling and coarse wrinkling in sun damaged skin. Histological studies have shown that long term (greater than 1 year) use of Tazarotene is associated with a significant reduction in atypical melanocytes and keratocytes - cells considered to be precursors of skin cancer. Some studies have shown long term use of Tazarotene to be associated with increased collagen production and better organization of skin collagen bundles.

Mechanism of action

Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors.

TargetActionsOrganism
ARetinoic acid receptor alpha
agonist
Human
ARetinoic acid receptor RXR-beta
agonist
Human
ARetinoic acid receptor gamma
agonist
Human
ARetinoic acid receptor beta
agonist
Human
Absorption

Minimal systemic absorption of tazarotene occurs due to its rapid metabolism in the skin to the active metabolite, tazarotenic acid, which can be systemically absorbed and further metabolized. Gender had no influence on the systemic bioavailability of tazarotenic acid.

Volume of distribution
Not Available
Protein binding

The active form of the drug, tazarotenic acid, is highly bound to plasma proteins (>99%).

Metabolism

Undergoes esterase hydrolysis in skin to form its active metabolite, tazarotenic acid. Tazarotenic acid is further metabolized in skin and, after systemic absorption, hepatically metabolized to sulfoxides, sulfones, and other polar products for elimination.

Route of elimination

Tazarotene and tazarotenic acid were metabolized to sulfoxides, sulfones and other polar metabolites which were eliminated through urinary and fecal pathways.

Half life

The half-life of the active form of the drug, tazarotenic acid, is approximately 18 hours in normal and psoriatic patients.

Clearance
Not Available
Toxicity

Excessive topical use may lead to marked redness, peeling, or discomfort. Oral ingestion of the drug may affect liver function causing hypertriglyceridemia. Other symptoms may include conjunctival irritation, hair loss, headache, edema, fatigue, dermatitis, nausea, and visual disturbances. Oral administration of this material to rats and rabbits at doses of 0.20 mg/kg/day (rabbits) and 0.25 mg/kg/day (rats) resulted in developmental toxicity. A no effect level of 0.05 mg/kg/day was established. Similar teratogenic effects have been reported for other retinoid compounds.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Tazarotene can be increased when it is combined with Abiraterone.Approved
CarbamazepineThe metabolism of Tazarotene can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Tazarotene can be decreased when combined with Celecoxib.Approved, Investigational
ClotrimazoleThe metabolism of Tazarotene can be decreased when combined with Clotrimazole.Approved, Vet Approved
CrisaboroleThe metabolism of Tazarotene can be decreased when combined with Crisaborole.Approved
DabrafenibThe serum concentration of Tazarotene can be decreased when it is combined with Dabrafenib.Approved
DeferasiroxThe serum concentration of Tazarotene can be increased when it is combined with Deferasirox.Approved, Investigational
EfavirenzThe metabolism of Tazarotene can be decreased when combined with Efavirenz.Approved, Investigational
FelodipineThe metabolism of Tazarotene can be decreased when combined with Felodipine.Approved, Investigational
FosphenytoinThe metabolism of Tazarotene can be increased when combined with Fosphenytoin.Approved
IrbesartanThe metabolism of Tazarotene can be decreased when combined with Irbesartan.Approved, Investigational
LapatinibThe metabolism of Tazarotene can be decreased when combined with Lapatinib.Approved, Investigational
LosartanThe metabolism of Tazarotene can be decreased when combined with Losartan.Approved
LumacaftorThe serum concentration of Tazarotene can be increased when it is combined with Lumacaftor.Approved
MifepristoneThe serum concentration of Tazarotene can be increased when it is combined with Mifepristone.Approved, Investigational
NilotinibThe metabolism of Tazarotene can be decreased when combined with Nilotinib.Approved, Investigational
PhenobarbitalThe metabolism of Tazarotene can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Tazarotene can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Tazarotene can be decreased when combined with Pioglitazone.Approved, Investigational
PrimidoneThe metabolism of Tazarotene can be increased when combined with Primidone.Approved, Vet Approved
QuinineThe metabolism of Tazarotene can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Tazarotene can be decreased when combined with Rabeprazole.Approved, Investigational
RifampicinThe metabolism of Tazarotene can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Tazarotene can be increased when combined with Rifapentine.Approved
RosiglitazoneThe metabolism of Tazarotene can be decreased when combined with Rosiglitazone.Approved, Investigational
SecobarbitalThe metabolism of Tazarotene can be increased when combined with Secobarbital.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Tazarotene can be decreased when combined with Sulfamethoxazole.Approved
TamoxifenThe metabolism of Tazarotene can be decreased when combined with Tamoxifen.Approved
TeriflunomideThe metabolism of Tazarotene can be decreased when combined with Teriflunomide.Approved
TopiroxostatThe metabolism of Tazarotene can be decreased when combined with Topiroxostat.Approved, Investigational
TrimethoprimThe metabolism of Tazarotene can be decreased when combined with Trimethoprim.Approved, Vet Approved
Food Interactions
Not Available

References

Synthesis Reference

Samuele Frigoli, Claudio Fuganti, Stefano Serra, Francesco Pizzocaro, Angelo Bedeschi, Paolo Tubertini, "Process for the preparation of Tazarotene." U.S. Patent US20060205950, issued September 14, 2006.

US20060205950
General References
Not Available
External Links
Human Metabolome Database
HMDB14937
KEGG Drug
D01132
KEGG Compound
C12531
PubChem Compound
5381
PubChem Substance
46508992
ChemSpider
5188
BindingDB
50265951
ChEBI
32184
ChEMBL
CHEMBL1657
Therapeutic Targets Database
DAP000462
PharmGKB
PA164746821
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tazarotene
ATC Codes
D05AX05 — Tazarotene
AHFS Codes
  • 84:92.00 — Misc. Skin and Mucous Membrane Agents
FDA label
Download (90.3 KB)
MSDS
Download (25.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceAcne Vulgaris3
1CompletedTreatmentAcne1
1CompletedTreatmentAcne Vulgaris1
1CompletedTreatmentPsoriasis1
1, 2Unknown StatusTreatmentCutaneous T-Cell Lymphoma (CTCL)1
2CompletedTreatmentAcne Vulgaris3
2CompletedTreatmentNail Psoriasis1
2CompletedTreatmentNeoplastic Syndrome1
2CompletedTreatmentPsoriasis1
2CompletedTreatmentSkin Carcinoma1
2Not Yet RecruitingTreatmentAcne Vulgaris1
2RecruitingTreatmentAcne Vulgaris1
2TerminatedTreatmentHand-foot Skin Reaction / Rash1
3CompletedTreatmentAcne Vulgaris3
3CompletedTreatmentPlaque Psoriasis3
3RecruitingTreatmentAcne Vulgaris1
3RecruitingTreatmentPlaque Psoriasis2
4CompletedTreatmentAcne Vulgaris3
4CompletedTreatmentOnychoclasis1
4TerminatedTreatmentAcne Vulgaris1
Not AvailableActive Not RecruitingTreatmentAtrophic Post Acne Scarring1
Not AvailableCompletedTreatmentActinic Keratosis (AK)1
Not AvailableCompletedTreatmentCancers / Hutchinson's Melanotic Freckle1
Not AvailableCompletedTreatmentRetinoid Intolerance / Sun-Damaged Skin1
Not AvailableSuspendedNot AvailablePlaque Psoriasis1

Pharmacoeconomics

Manufacturers
  • Allergan inc
Packagers
Dosage forms
FormRouteStrength
Aerosol, foamTopical1 mg/g
CreamTopical.5 mg/g
CreamTopical1 mg/g
CreamCutaneous.5 mg/g
CreamCutaneous1 mg/g
CreamTopical0.05 %
CreamTopical0.1 %
GelCutaneous.5 mg/g
GelCutaneous1 mg/g
GelOral1 mg/g
GelTopical0.05 %
GelTopical0.1 %
Prices
Unit descriptionCostUnit
Tazorac 0.1% Gel 100 gm Tube638.75USD tube
Tazorac 0.05% Gel 100 gm Tube601.14USD tube
Tazorac 60 gm Tube .1% 60 gm Tube383.22USD tube
Tazorac 60 gm Tube .05% 60 gm Tube360.72USD tube
Tazorac 0.1% Gel 30 gm Tube191.64USD tube
Tazorac 30 gm Tube .1% 30 gm Tube191.64USD tube
Tazorac 0.05% Cream 30 gm Tube180.39USD tube
Tazorac 0.05% Gel 30 gm Tube180.39USD tube
Tazorac 0.1% cream5.59USD g
Tazorac 0.05% cream5.26USD g
Tazorac 0.05 % Gel1.49USD g
Tazorac 0.1 % Gel1.49USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5914334No1994-06-072014-06-07Us
US5089509No1994-06-132011-06-13Us
CA2191773No2004-08-102015-08-10Canada
US8808716No2010-02-242030-02-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP5.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00075 mg/mLALOGPS
logP5.15ALOGPS
logP5.22ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)1.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.88 m3·mol-1ChemAxon
Polarizability40.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9936
Blood Brain Barrier+0.9675
Caco-2 permeable+0.5233
P-glycoprotein substrateSubstrate0.5758
P-glycoprotein inhibitor IInhibitor0.5422
P-glycoprotein inhibitor IINon-inhibitor0.5926
Renal organic cation transporterNon-inhibitor0.8219
CYP450 2C9 substrateNon-substrate0.7308
CYP450 2D6 substrateNon-substrate0.7687
CYP450 3A4 substrateSubstrate0.5187
CYP450 1A2 substrateInhibitor0.6172
CYP450 2C9 inhibitorInhibitor0.6385
CYP450 2D6 inhibitorNon-inhibitor0.8531
CYP450 2C19 inhibitorInhibitor0.6586
CYP450 3A4 inhibitorNon-inhibitor0.6387
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6124
Ames testNon AMES toxic0.8154
CarcinogenicityNon-carcinogens0.8925
BiodegradationNot ready biodegradable0.9946
Rat acute toxicity2.5435 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.7757
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uk9-0129000000-2db71aa7cf68c539db6d

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Retinoids
Direct Parent
Retinoids
Alternative Parents
Thiochromanes / Pyridinecarboxylic acids / 1-benzothiopyrans / Alkylarylthioethers / Thiopyrans / Benzenoids / Heteroaromatic compounds / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds
show 5 more
Substituents
Tazarotene / Thiochromane / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Benzothiopyran / 1-benzothiopyran / Aryl thioether / Alkylarylthioether / Pyridine / Thiopyran
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
ethyl ester, retinoid, pyridines, acetylenic compound, thiochromane (CHEBI:32184)

Targets

Kind
Protein
Organism
Human
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. Baumann L, Vujevich J, Halem M, Martin LK, Kerdel F, Lazarus M, Pacheco H, Black L, Bryde J: Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. Cutis. 2005 Jul;76(1):69-73. [PubMed:16144296]
  2. Chandraratna RA: Tazarotene--first of a new generation of receptor-selective retinoids. Br J Dermatol. 1996 Oct;135 Suppl 49:18-25. [PubMed:9035701]
  3. Yen A, Fenning R, Chandraratna R, Walker P, Varvayanis S: A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation. Mol Pharmacol. 2004 Dec;66(6):1727-37. Epub 2004 Sep 21. [PubMed:15383624]
  4. Meder W, Wendland M, Busmann A, Kutzleb C, Spodsberg N, John H, Richter R, Schleuder D, Meyer M, Forssmann WG: Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. FEBS Lett. 2003 Dec 18;555(3):495-9. [PubMed:14675762]
  5. Wang Q, Lee D, Sysounthone V, Chandraratna RAS, Christakos S, Korah R, Wieder R: 1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects. Breast Cancer Res Treat. 2001 May;67(2):157-68. [PubMed:11519864]
  6. Nagpal S, Chandraratna RA: Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31. [PubMed:10828316]
Kind
Protein
Organism
Human
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Nagpal S, Chandraratna RA: Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31. [PubMed:10828316]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
  4. Arechalde A, Saurat JH: Management of psoriasis: the position of retinoid drugs. BioDrugs. 2000 May;13(5):327-33. [PubMed:18034539]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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. Jones PH, Burnett RD, Fainaru I, Nadolny P, Walker P, Yu Z, Tang-Liu D, Ganesan TS, Talbot DC, Harris AL, Rustin GJ: A phase 1 study of tazarotene in adults with advanced cancer. Br J Cancer. 2003 Sep 1;89(5):808-15. [PubMed:12942109]
  2. Orlandi A, Bianchi L, Costanzo A, Campione E, Giusto Spagnoli L, Chimenti S: Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene. J Invest Dermatol. 2004 Apr;122(4):1037-41. [PubMed:15102095]
  3. Chandraratna RA: Tazarotene--first of a new generation of receptor-selective retinoids. Br J Dermatol. 1996 Oct;135 Suppl 49:18-25. [PubMed:9035701]
  4. Arechalde A, Saurat JH: Management of psoriasis: the position of retinoid drugs. BioDrugs. 2000 May;13(5):327-33. [PubMed:18034539]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18