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

Stem definitionDrug idCAS RN
retinol derivatives 2722 302-79-4

Description:

MoleculeDescription

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:

PropertyValueReference
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
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.70 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Oct. 20, 1971 FDA VALEANT INTL

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Differentiation syndrome 401.13 57.09 47 340 113 2357585
Febrile neutropenia 101.02 57.09 27 360 10855 2346843
Thrombocytopenia 73.53 57.09 24 363 19107 2338591
Neutropenia 66.79 57.09 23 364 21525 2336173
Oral herpes 65.24 57.09 14 373 2188 2355510
Neutropenic sepsis 65.09 57.09 13 374 1429 2356269
Leukaemia recurrent 64.83 57.09 10 377 242 2357456
Haematopoietic neoplasm 63.09 57.09 7 380 7 2357691
Mucosal inflammation 58.06 57.09 15 372 5209 2352489
Product use issue 57.93 57.09 18 369 12151 2345547
Intracranial pressure increased 57.39 57.09 11 376 975 2356723

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Differentiation syndrome 334.00 75.98 42 310 128 1746301
Acute myeloid leukaemia 124.39 75.98 27 325 3014 1743415
Febrile neutropenia 102.90 75.98 30 322 11070 1735359
Haematopoietic neoplasm 95.77 75.98 11 341 9 1746420
Neutropenia 92.18 75.98 31 321 18229 1728200
Leukaemia recurrent 80.24 75.98 13 339 286 1746143
Lymphopenia 77.05 75.98 17 335 2016 1744413
Cytogenetic abnormality 76.08 75.98 12 340 221 1746208

Pharmacologic Action:

SourceCodeDescription
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 L01XX14 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Other antineoplastic agents
FDA EPC N0000175607 Retinoid
FDA CS M0018962 Retinoids
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:50176 keratolytic drug
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:67198 retinoic acid receptor agonist
MeSH PA D000970 Antineoplastic Agents
MeSH PA D003879 Dermatologic Agents
MeSH PA D007641 Keratolytic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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
Keratosis follicularis off-label use 48611009 DOID:2734
Lamellar ichthyosis off-label use 205550003
Plane wart off-label use 240539000
Primary cutaneous T-cell lymphoma off-label use 400122007
Severe Recalcitrant Nodular Rosacea off-label use
Osteomalacia contraindication 4598005 DOID:10573
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Rectal hemorrhage contraindication 12063002
Hypercholesterolemia contraindication 13644009
Hearing loss contraindication 15188001
Agranulocytosis contraindication 17182001 DOID:12987
Myocardial infarction contraindication 22298006 DOID:5844
Sunburn contraindication 23346002
Atopic dermatitis contraindication 24079001 DOID:3310
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Crohn's disease contraindication 34000006
Depressive disorder contraindication 35489007
Eczema contraindication 43116000
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Vitiligo contraindication 56727007 DOID:12306
Anorexia nervosa contraindication 56882008 DOID:8689
Tinnitus contraindication 60862001
Corneal opacity contraindication 64634000
Ulcerative colitis contraindication 64766004 DOID:8577
Osteoporosis contraindication 64859006 DOID:11476
Benign intracranial hypertension contraindication 68267002 DOID:11459
Psychotic disorder contraindication 69322001
Diabetes mellitus contraindication 73211009 DOID:9351
Disorder of bone contraindication 76069003 DOID:0080001
Congenital neutropenia contraindication 89655007
Kidney disease contraindication 90708001 DOID:557
Venous thrombosis contraindication 111293003
Leukocytosis contraindication 111583006
Mycosis fungoides contraindication 118618005
Inflammatory disease of liver contraindication 128241005
Bleeding contraindication 131148009
Liver function tests abnormal contraindication 166603001
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Telangiectasia disorder contraindication 247479008
Dyspnea contraindication 267036007
Edema contraindication 267038008
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Keratoconjunctivitis sicca contraindication 302896008 DOID:12895
Neutropenic disorder contraindication 303011007 DOID:1227
Pericardial effusion contraindication 373945007 DOID:118
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Fever contraindication 386661006
Pseudomembranous enterocolitis contraindication 397683000
Atrophoderma contraindication 399979006
Peripheral vascular disease contraindication 400047006
Severe diarrhea contraindication 409587002
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Denuded skin contraindication 418242004
Retinoic acid syndrome contraindication 450887006
Pulmonary Infiltrates contraindication
Pleural Effusions contraindication
Predisposition To Hypertriglyceridemia contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.17 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.025% ZIANA MEDICIS N050802 Nov. 7, 2006 RX GEL TOPICAL 6387383 Aug. 3, 2020 TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 12 YEARS OR OLDER
0.05% ALTRENO DOW PHARM N209353 Aug. 23, 2018 RX LOTION TOPICAL 6517847 Aug. 3, 2020 TOPICAL TREATMENT OF ACNE VULGARIS IN PATIENTS 9 YEARS OF AGE AND OLDER

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.05% ALTRENO DOW PHARM N209353 Aug. 23, 2018 RX LOTION TOPICAL Aug. 23, 2021 NEW DOSAGE FORM

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Retinoic acid receptor gamma Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
Retinoic acid receptor beta Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor AGONIST EC50 6.70 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 6.64 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.53 DRUG MATRIX
Mitogen-activated protein kinase 1 Kinase IC50 6.24 DRUG MATRIX
Retinoic acid receptor RXR-beta Nuclear hormone receptor Ki 9.30 CHEMBL
Retinoic acid receptor RXR-alpha Nuclear hormone receptor Ki 9.40 CHEMBL
Retinoic acid receptor RXR-gamma Nuclear hormone receptor Ki 8.85 CHEMBL
11-cis retinol dehydrogenase Enzyme Ki 7 WOMBAT-PK
Nuclear receptor ROR-beta Nuclear hormone receptor ANTAGONIST IC50 9.82 IUPHAR
Peroxisome proliferator-activated receptor delta Nuclear hormone receptor AGONIST Kd 7.80 IUPHAR
Nuclear receptor ROR-gamma Nuclear hormone receptor IC50 6.70 CHEMBL
Nuclear receptor ROR-alpha Nuclear hormone receptor IC50 6.70 CHEMBL
Nuclear receptor subfamily 2 group C member 2 Unclassified AGONIST EC50 4.62 IUPHAR
Retinoic acid receptor alpha Transcription factor Kd 7.82 CHEMBL
Retinoic acid receptor RXR-gamma Transcription factor Kd 6.46 CHEMBL
Retinoic acid receptor RXR-beta Transcription factor Kd 6.51 CHEMBL
Retinoic acid receptor gamma Transcription factor Kd 7.74 CHEMBL
Cellular retinoic acid-binding protein 1 Cytosolic other IC50 6.43 CHEMBL
Retinoic acid receptor RXR-alpha Transcription factor Kd 6 CHEMBL
Cellular retinoic acid-binding protein 1 Cytosolic other Kd 9.40 CHEMBL
Retinoic acid receptor beta Transcription factor Kd 7.89 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 4.54 CHEMBL
Cellular retinoic acid-binding protein 2 Cytosolic other Kd 8.70 CHEMBL

External reference:

IDSource
4018550 VUID
N0000146871 NUI
C0040845 UMLSCUI
D00094 KEGG_DRUG
5688UTC01R UNII
2875 INN_ID
54972005 SNOMEDCT_US
4018550 VANDF
10753 RXNORM
387305002 SNOMEDCT_US
46802 MMSL
5610 MMSL
d03863 MMSL
001954 NDDF
CHEBI:15367 CHEBI
CHEMBL38 ChEMBL_ID
DB00755 DRUGBANK_ID
REA PDB_CHEM_ID
444795 PUBCHEM_CID
D014212 MESH_DESCRIPTOR_UI
2644 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Altreno HUMAN PRESCRIPTION DRUG LABEL 1 0187-0005 LOTION 0.50 mg TOPICAL NDA 15 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5140 GEL 1 mg TOPICAL NDA 17 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5144 GEL 0.40 mg TOPICAL NDA 17 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5146 GEL 0.60 mg TOPICAL NDA 17 sections
Retin-A MICRO HUMAN PRESCRIPTION DRUG LABEL 1 0187-5148 GEL 0.80 mg TOPICAL NDA 17 sections
Renova HUMAN PRESCRIPTION DRUG LABEL 1 0187-5150 CREAM 0.20 mg TOPICAL NDA 13 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5160 CREAM 0.25 mg TOPICAL NDA 12 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5162 CREAM 0.50 mg TOPICAL NDA 12 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5164 CREAM 1 mg TOPICAL NDA 12 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5170 GEL 0.25 mg TOPICAL NDA 12 sections
Retin-A HUMAN PRESCRIPTION DRUG LABEL 1 0187-5172 GEL 0.10 mg TOPICAL NDA 12 sections
TRI-LUMA HUMAN PRESCRIPTION DRUG LABEL 3 0299-5950 CREAM 0.50 mg TOPICAL NDA 15 sections
Avita HUMAN PRESCRIPTION DRUG LABEL 1 0378-6140 GEL 0.25 mg TOPICAL NDA 13 sections
Avita HUMAN PRESCRIPTION DRUG LABEL 1 0378-6141 CREAM 0.25 mg TOPICAL NDA 12 sections
Tretionin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8082 CREAM 0.25 mg TOPICAL NDA authorized generic 11 sections
Tretionin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8083 CREAM 0.50 mg TOPICAL NDA authorized generic 11 sections
Tretionin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8084 CREAM 1 mg TOPICAL NDA authorized generic 11 sections
Tretionin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8085 GEL 0.10 mg TOPICAL NDA authorized generic 11 sections
Tretionin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8086 GEL 0.25 mg TOPICAL NDA authorized generic 11 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8090 GEL 0.50 mg TOPICAL ANDA 15 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8092 GEL 0.40 mg TOPICAL NDA authorized generic 16 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0378-8093 GEL 1 mg TOPICAL NDA authorized generic 16 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0472-0117 CREAM 0.25 mg TOPICAL NDA AUTHORIZED GENERIC 13 sections
Clindamycin Phosphate and Tretinoin HUMAN PRESCRIPTION DRUG LABEL 2 0472-1790 GEL 0.25 mg TOPICAL ANDA 15 sections
Tretinoin HUMAN PRESCRIPTION DRUG LABEL 1 0555-0808 CAPSULE, LIQUID FILLED 10 mg ORAL ANDA 13 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2201 CREAM 1 mg TOPICAL ANDA 14 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2205 CREAM 0.50 mg TOPICAL ANDA 14 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2225 CREAM 0.25 mg TOPICAL ANDA 14 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2301 GEL 0.10 mg TOPICAL ANDA 14 sections
TRETINOIN HUMAN PRESCRIPTION DRUG LABEL 1 0574-2325 GEL 0.25 mg TOPICAL ANDA 14 sections