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

Stem definition	Drug id	CAS RN
retinol derivatives	2722	302-79-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: tretinoin potassium trans-Retinoic acid tretinoin sodium retinoic acid tretinoin	An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE). 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:

tretinoin potassium
trans-Retinoic acid
tretinoin sodium
retinoic acid
tretinoin

An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).

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:

None

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	3.70 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
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

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Approvals:

Date	Agency	Company	Orphan
Oct. 20, 1971	FDA	VALEANT INTL

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
Differentiation syndrome	792.01	16.14	135	8037	968	63479882
Blepharospasm	260.21	16.14	73	8099	5923	63474927
Taste disorder	197.34	16.14	72	8100	13590	63467260
Epilepsy	152.87	16.14	73	8099	26992	63453858
Idiopathic intracranial hypertension	137.74	16.14	38	8134	2893	63477957
Product use in unapproved indication	131.03	16.14	137	8035	178943	63301907
Intracranial pressure increased	96.20	16.14	33	8139	5194	63475656
Migraine	86.27	16.14	85	8087	103261	63377589
Gastrooesophageal reflux disease	86.11	16.14	82	8090	95557	63385293
Memory impairment	78.32	16.14	81	8091	104177	63376673

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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
Differentiation syndrome	979.14	26.54	157	2671	1281	34952822
Idiopathic intracranial hypertension	203.09	26.54	37	2791	664	34953439
Hyperleukocytosis	121.75	26.54	29	2799	1973	34952130
Electrocardiogram QT prolonged	109.00	26.54	57	2771	40895	34913208
Haematopoietic neoplasm	82.61	26.54	12	2816	44	34954059
Acute myeloid leukaemia	77.44	26.54	35	2793	18235	34935868
Product use in unapproved indication	75.92	26.54	68	2760	117431	34836672
Leukaemia recurrent	70.85	26.54	18	2810	1597	34952506
Cytogenetic abnormality	54.58	26.54	13	2815	882	34953221
Hypokalaemia	46.25	26.54	38	2790	58176	34895927

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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
Differentiation syndrome	1705.40	16.46	288	8840	2236	79733024
Idiopathic intracranial hypertension	261.44	16.46	63	9065	3159	79732101
Blepharospasm	179.49	16.46	53	9075	5798	79729462
Myelodysplastic syndrome transformation	160.32	16.46	32	9096	657	79734603
Product use in unapproved indication	139.60	16.46	157	8971	250202	79485058
Taste disorder	127.90	16.46	53	9075	15770	79719490
Hyperleukocytosis	127.33	16.46	34	9094	2576	79732684
Leukaemia recurrent	106.82	16.46	30	9098	2744	79732516
Intracranial pressure increased	85.00	16.46	33	9095	8289	79726971
Acute myeloid leukaemia	78.25	16.46	47	9081	30838	79704422

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D10AD01	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR TOPICAL USE Retinoids for topical use in acne
ATC	D10AD51	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR TOPICAL USE Retinoids for topical use in acne
ATC	L01XF01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS OTHER ANTINEOPLASTIC AGENTS Retinoids for cancer treatment
CHEBI has role	CHEBI:22586	antioxidants
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50176	keratolytic drugs
CHEBI has role	CHEBI:62488	signal molecules
CHEBI has role	CHEBI:63794	retinoid X receptor agonists
CHEBI has role	CHEBI:67079	anti-inflammatory agents
CHEBI has role	CHEBI:67198	retinoic acid receptor agonists

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

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Disease	Relation	SNOMED_ID
Chloasma	indication	36209000
Acne vulgaris	indication	88616000
Acute promyelocytic leukemia, FAB M3	indication	110004001
Hyperkeratosis	indication	396228006
Facial Fine Wrinkling	indication
Solar Lentigines	indication
Fine Wrinkling	indication
Severe Recalcitrant Nodular Acne	indication
Kaposi's Sarcoma Skin Lesions	indication
Mottle Hyperpigmentation	indication

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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)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.05%	ALTRENO	DOW PHARM	N209353	Aug. 23, 2018	RX	LOTION	TOPICAL	10653656	Aug. 22, 2038	TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 9 YEARS OF AGE AND OLDER
0.05%	ALTRENO	DOW PHARM	N209353	Aug. 23, 2018	RX	LOTION	TOPICAL	11324710	Aug. 22, 2038	TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1%	TWYNEO	GALDERMA LABS LP	N214902	July 26, 2021	RX	CREAM	TOPICAL	9868103	Aug. 8, 2028	TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1%	TWYNEO	GALDERMA LABS LP	N214902	July 26, 2021	RX	CREAM	TOPICAL	10653899	Dec. 30, 2030	TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER
3%;0.1%	TWYNEO	GALDERMA LABS LP	N214902	July 26, 2021	RX	CREAM	TOPICAL	10420743	July 12, 2038	TOPICAL TREATMENT OF ACNE VULGARIS IN ADULTS AND PEDIATRIC PATIENTS 9 YEARS OF AGE AND OLDER

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
3%;0.1%	TWYNEO	GALDERMA LABS LP	N214902	July 26, 2021	RX	CREAM	TOPICAL	July 26, 2024	NEW COMBINATION

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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	AGONIST	EC50	6.70	WOMBAT-PK	CHEMBL
Retinoic acid receptor gamma	Nuclear hormone receptor	P13631	RARG_HUMAN	AGONIST	EC50	6.70	WOMBAT-PK	CHEMBL
Retinoic acid receptor alpha	Nuclear hormone receptor	P10276	RARA_HUMAN	AGONIST	EC50	6.70	WOMBAT-PK	CHEMBL
Nuclear receptor ROR-alpha	Nuclear hormone receptor	P35398	RORA_HUMAN		IC50	6.70	CHEMBL
Retinoic acid receptor RXR-alpha	Nuclear hormone receptor	P19793	RXRA_HUMAN		Ki	9.40	CHEMBL
Retinoic acid receptor RXR-beta	Nuclear hormone receptor	P28702	RXRB_HUMAN		Ki	9.30	CHEMBL
Retinoic acid receptor RXR-gamma	Nuclear hormone receptor	P48443	RXRG_HUMAN		Ki	8.85	CHEMBL
Peroxisome proliferator-activated receptor delta	Nuclear hormone receptor	Q03181	PPARD_HUMAN	AGONIST	Kd	7.80	IUPHAR
Nuclear receptor ROR-beta	Nuclear hormone receptor	Q92753	RORB_HUMAN	ANTAGONIST	IC50	9.82	IUPHAR
Nuclear receptor ROR-gamma	Nuclear hormone receptor	P51449	RORG_HUMAN		IC50	6.70	CHEMBL

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External reference:

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ID	Source
3KV	PDB_CHEM_ID
001954	NDDF
10753	RXNORM
2644	IUPHAR_LIGAND_ID
2875	INN_ID
387305002	SNOMEDCT_US
4018550	VUID
4018550	VANDF
444795	PUBCHEM_CID
46802	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Altreno	HUMAN PRESCRIPTION DRUG LABEL	1	0187-0005	LOTION	0.50 mg	TOPICAL	NDA	24 sections
Avita	HUMAN PRESCRIPTION DRUG LABEL	1	0378-6140	GEL	0.25 mg	TOPICAL	NDA	22 sections
Renova	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5150	CREAM	0.20 mg	TOPICAL	NDA	25 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5160	CREAM	0.25 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5160	CREAM	0.25 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5162	CREAM	0.50 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5162	CREAM	0.50 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5164	CREAM	1 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5164	CREAM	1 mg	TOPICAL	NDA	21 sections
Retin-A	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5170	GEL	0.25 mg	TOPICAL	NDA	21 sections

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