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

Stem definitionDrug idCAS RN
retinol derivatives 78 55079-83-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acitretin
  • acitretinoin
  • etretin
  • neotigason
  • soriatane
  • isoacitretin
  • isoetretin
An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of ETRETINATE with the advantage of a much shorter half-life when compared with etretinate.
  • Molecular weight: 326.44
  • Formula: C21H26O3
  • CLOGP: 6.07
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -5.83
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
35 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.83 ┬ÁM/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 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 59 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Oct. 28, 1996 FDA STIEFEL LABS INC

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
Pregnancy 174.33 43.17 41 444 7908 2349692
Exposure during pregnancy 148.44 43.17 46 439 25173 2332427
Psoriasis 138.86 43.17 40 445 16968 2340632
Drug exposure before pregnancy 90.32 43.17 14 471 277 2357323
Abortion induced 87.00 43.17 20 465 3416 2354184
Erythema 76.25 43.17 28 457 25131 2332469
Alopecia 72.28 43.17 26 459 21975 2335625
Drug ineffective 61.56 43.17 37 448 101587 2256013
Skin exfoliation 57.69 43.17 16 469 5774 2351826
Maternal exposure before pregnancy 56.38 43.17 11 474 849 2356751
Decreased appetite 48.37 43.17 21 464 28870 2328730
Type IIb hyperlipidaemia 44.44 43.17 5 480 4 2357596
Pustular psoriasis 44.06 43.17 9 476 875 2356725
Pregnancy of partner 43.35 43.17 6 479 51 2357549

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
Vein rupture 300.91 60.12 37 512 41 1746191
Psoriasis 300.86 60.12 77 472 11548 1734684
Drug ineffective 283.74 60.12 109 440 63692 1682540
Injection site haemorrhage 175.02 60.12 38 511 2699 1743533
Myalgia 153.78 60.12 49 500 15609 1730623
Injection site swelling 152.02 60.12 35 514 3236 1742996
Pain in extremity 149.83 60.12 50 499 18422 1727810
Muscular weakness 142.71 60.12 42 507 10207 1736025
Venous injury 135.57 60.12 18 531 50 1746182
Insomnia 131.55 60.12 44 505 16232 1730000
Headache 129.85 60.12 53 496 34323 1711909
Injection site papule 96.47 60.12 14 535 86 1746146
Skin plaque 83.56 60.12 17 532 863 1745369
Nausea 82.84 60.12 44 505 51152 1695080
Granuloma annulare 80.74 60.12 11 538 39 1746193
Erythema 71.04 60.12 27 522 14161 1732071
Induration 64.01 60.12 11 538 218 1746014
Condition aggravated 60.61 60.12 27 522 21123 1725109
Skin exfoliation 60.19 60.12 18 531 4517 1741715

Pharmacologic Action:

SourceCodeDescription
ATC D05BB02 DERMATOLOGICALS
ANTIPSORIATICS
ANTIPSORIATICS FOR SYSTEMIC USE
Retinoids for treatment of psoriasis
FDA EPC N0000175607 Retinoid
FDA Chemical/Ingredient N0000007700 Retinoids
CHEBI has role CHEBI:50176 keratolytic drug
MeSH PA D003879 Dermatologic Agents
MeSH PA D007641 Keratolytic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Severe Recalcitrant Psoriasis indication
Lichen planus off-label use 4776004 DOID:9201
Keratosis follicularis off-label use 48611009 DOID:2734
Lamellar ichthyosis off-label use 205550003
Ichthyosiform erythroderma off-label use 268282005
Primary cutaneous T-cell lymphoma off-label use 400122007
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Depressive disorder contraindication 35489007
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Night blindness contraindication 65194006 DOID:8499
Benign intracranial hypertension contraindication 68267002 DOID:11459
Diabetes mellitus contraindication 73211009 DOID:9351
Premature epiphyseal closure contraindication 89493005
Liver function tests abnormal contraindication 166603001
Hypoalphalipoproteinemia contraindication 190785000
Acute pancreatitis contraindication 197456007 DOID:2913
Hypertrophy of bone contraindication 203514008 DOID:205
Drug-induced hepatitis contraindication 235876009
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Cardiovascular event risk contraindication 395112001
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Psychiatric Disturbance 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)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Retinoic acid receptor alpha Nuclear hormone receptor AGONIST WOMBAT-PK CHEMBL
Retinoic acid receptor gamma Nuclear hormone receptor AGONIST CHEMBL CHEMBL
Bile salt export pump Transporter IC50 4.74 CHEMBL
Bile salt export pump Unclassified IC50 4.71 CHEMBL

External reference:

IDSource
4021061 VUID
N0000148524 NUI
C0050559 UMLSCUI
D02754 KEGG_DRUG
108914001 SNOMEDCT_US
4021061 VANDF
16818 RXNORM
386938006 SNOMEDCT_US
4128 MMSL
d03836 MMSL
117161 MMSL
004121 NDDF
BK59Y5A02O UNII
69427-46-9 SECONDARY_CAS_RN
CHEMBL1131 ChEMBL_ID
DB00459 DRUGBANK_ID
5530 INN_ID
CHEBI:50173 CHEBI
7598 IUPHAR_LIGAND_ID
5284513 PUBCHEM_CID
D017255 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1135 CAPSULE 10 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1136 CAPSULE 25 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1138 CAPSULE 17.50 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1667 CAPSULE 10 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1668 CAPSULE 17.50 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1669 CAPSULE 25 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1698 CAPSULE 22.50 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1750 CAPSULE 10 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1751 CAPSULE 17.50 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1752 CAPSULE 22.50 mg ORAL ANDA 17 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0115-1753 CAPSULE 25 mg ORAL ANDA 17 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 0145-0090 CAPSULE 10 mg ORAL NDA 16 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 0145-0091 CAPSULE 25 mg ORAL NDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0378-7020 CAPSULE 10 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0378-7023 CAPSULE 25 mg ORAL ANDA 16 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-086 CAPSULE 10 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-087 CAPSULE 17.50 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-088 CAPSULE 25 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-080 CAPSULE 10 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-081 CAPSULE 17.50 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-083 CAPSULE 25 mg ORAL ANDA 14 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 66993-894 CAPSULE 10 mg ORAL NDA authorized generic 15 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 66993-896 CAPSULE 25 mg ORAL NDA authorized generic 15 sections