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isotretinoin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
retinol derivatives	1508	4759-48-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: isotretinoin 13-cis-retinoic acid 13-cis-vitamin A acid accure accutane isotrex neovitamin A acid roaccutan roaccutane	A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects. Molecular weight: 300.44 Formula: C20H28O2 CLOGP: 6.74 LIPINSKI: 1 HAC: 2 HDO: 1 TPSA: 37.30 ALOGS: -4.80 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

isotretinoin
13-cis-retinoic acid
13-cis-vitamin A acid
accure
accutane
isotrex
neovitamin A acid
roaccutan
roaccutane

A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.

Molecular weight: 300.44
Formula: C20H28O2
CLOGP: 6.74
LIPINSKI: 1
HAC: 2
HDO: 1
TPSA: 37.30
ALOGS: -4.80
ROTB: 5

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
30	mg	O

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	6.66 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	40 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
May 7, 1982	FDA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Unintended pregnancy	7827.01	21.81	1461	25348	4718	63457495
Abortion induced	3397.70	21.81	801	26008	9441	63452772
Exposure during pregnancy	3173.84	21.81	1461	25348	154086	63308127
Pregnancy	1814.37	21.81	654	26155	36182	63426031
Depression	1638.84	21.81	1020	25789	195472	63266741
Blood triglycerides increased	1266.25	21.81	383	26426	12105	63450108
Mood altered	1195.35	21.81	381	26428	14362	63447851
Treatment noncompliance	1186.48	21.81	482	26327	36843	63425370
Dry skin	922.67	21.81	459	26350	56428	63405785
Suicidal ideation	797.18	21.81	429	26380	61992	63400221

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Depression	1708.64	20.80	855	15730	96243	34844103
Mood altered	1327.20	20.80	378	16207	8574	34931772
Suicidal ideation	1216.63	20.80	518	16067	39870	34900476
Lip dry	1088.82	20.80	221	16364	1033	34939313
Blood triglycerides increased	754.71	20.80	275	16310	13884	34926462
Dry skin	711.36	20.80	330	16255	30957	34909389
Mood swings	483.04	20.80	170	16415	7731	34932615
Cheilitis	390.10	20.80	109	16476	2282	34938064
Acne fulminans	343.53	20.80	63	16522	147	34940199
Chapped lips	319.43	20.80	71	16514	545	34939801

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Unintended pregnancy	4422.48	19.50	832	30141	3101	79710314
Exposure during pregnancy	2782.55	19.50	1147	29826	99985	79613430
Abortion induced	2095.83	19.50	498	30475	6611	79706804
Depression	2082.06	19.50	1196	29777	215594	79497821
Blood triglycerides increased	1610.45	19.50	510	30463	20530	79692885
Mood altered	1530.69	19.50	472	30501	17375	79696040
Treatment noncompliance	1477.98	19.50	606	30367	51662	79661753
Suicidal ideation	1260.63	19.50	607	30366	75733	79637682
Dry skin	1156.88	19.50	552	30421	67443	79645972
Lip dry	960.71	19.50	320	30653	15098	79698317

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D10AD04	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR TOPICAL USE Retinoids for topical use in acne
ATC	D10AD54	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR TOPICAL USE Retinoids for topical use in acne
ATC	D10BA01	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR SYSTEMIC USE Retinoids for treatment of acne
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50176	keratolytic drugs
CHEBI has role	CHEBI:50905	teratogeno
FDA CS	M0018962	Retinoids
FDA EPC	N0000175607	Retinoid
MeSH PA	D003879	Dermatologic Agents
MeSH PA	D009676	Noxae

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Hypertensive disorder	indication	38341003	DOID:10763
Severe Recalcitrant Nodular Acne	indication
Primary cutaneous T-cell lymphoma	off-label use	400122007
Severe Recalcitrant Nodular Rosacea	off-label use
Anuria	contraindication	2472002	DOID:2983
Osteomalacia	contraindication	4598005	DOID:10573
Suicidal thoughts	contraindication	6471006
Alcoholism	contraindication	7200002
Rectal hemorrhage	contraindication	12063002
Hypercholesterolemia	contraindication	13644009

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.17	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Retinoic acid receptor beta	Nuclear hormone receptor	P10826	RARB_HUMAN	INHIBITOR			CHEMBL	CHEMBL
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN		Ki	5.52	DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		Ki	5.63	DRUG MATRIX
Retinoic acid receptor alpha	Nuclear hormone receptor	P10276	RARA_HUMAN		ED50	8.23	WOMBAT-PK
Alcohol dehydrogenase 4	Enzyme	P08319	ADH4_HUMAN		Ki	5.52	WOMBAT-PK
Dehydrogenase/reductase SDR family member 9	Enzyme	Q9BPW9	DHRS9_HUMAN		Ki	4.52	WOMBAT-PK
11-cis retinol dehydrogenase	Enzyme	Q92781	RDH1_HUMAN		Ki	7	WOMBAT-PK
17-beta-hydroxysteroid dehydrogenase type 6	Enzyme	O14756	H17B6_HUMAN		Ki	5.40	WOMBAT-PK
Mitogen-activated protein kinase 14	Kinase	Q16539	MK14_HUMAN		IC50	5.60	DRUG MATRIX
Mitogen-activated protein kinase 1	Kinase	P28482	MK01_HUMAN		IC50	6.34	DRUG MATRIX

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External reference:

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ID	Source
001961	NDDF
202795	RXNORM
38314008	SNOMEDCT_US
387208003	SNOMEDCT_US
3KV	PDB_CHEM_ID
4017801	VUID
4017801	VANDF
4617	INN_ID
4937	MMSL
5282379	PUBCHEM_CID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6611	CAPSULE	10 mg	ORAL	ANDA	25 sections
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6611	CAPSULE	10 mg	ORAL	ANDA	25 sections
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6612	CAPSULE	20 mg	ORAL	ANDA	25 sections
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6612	CAPSULE	20 mg	ORAL	ANDA	25 sections
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6614	CAPSULE	40 mg	ORAL	ANDA	25 sections
Amnesteem	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6614	CAPSULE	40 mg	ORAL	ANDA	25 sections
Claravis	HUMAN PRESCRIPTION DRUG LABEL	1	0555-1054	CAPSULE, LIQUID FILLED	10 mg	ORAL	ANDA	23 sections
Claravis	HUMAN PRESCRIPTION DRUG LABEL	1	0555-1054	CAPSULE, LIQUID FILLED	10 mg	ORAL	ANDA	23 sections
Claravis	HUMAN PRESCRIPTION DRUG LABEL	1	0555-1055	CAPSULE, LIQUID FILLED	20 mg	ORAL	ANDA	23 sections
Claravis	HUMAN PRESCRIPTION DRUG LABEL	1	0555-1055	CAPSULE, LIQUID FILLED	20 mg	ORAL	ANDA	23 sections

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