acitretin indications/contra

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

Drug dosage:

DoseUnitRoute
35 mg O

Approvals:

DateAgencyCompanyOrphan
Oct. 28, 1996 FDA STIEFEL LABS INC

FDA Adverse Event Reporting System

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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 203.56 38.09 48 713 7832 3377266
Psoriasis 189.17 38.09 55 706 20293 3364805
Exposure during pregnancy 144.08 38.09 48 713 27515 3357583
Maternal exposure before pregnancy 139.01 38.09 25 736 1051 3384047
Erythema 126.29 38.09 44 717 28766 3356332
Drug ineffective 113.04 38.09 61 700 116029 3269069
Abortion induced 92.44 38.09 22 739 3669 3381429
Granuloma annulare 72.51 38.09 11 750 156 3384942
Condition aggravated 62.56 38.09 29 732 39204 3345894
Dermatitis exfoliative 61.67 38.09 15 746 2728 3382370
Induration 61.59 38.09 11 750 440 3384658
Pregnancy of partner 60.97 38.09 10 751 239 3384859
Alopecia 60.50 38.09 23 738 18963 3366135
Myalgia 58.34 38.09 26 735 32049 3353049
Pustular psoriasis 58.25 38.09 12 749 1027 3384071
Skin plaque 57.79 38.09 13 748 1685 3383413
Cushing's syndrome 57.08 38.09 12 749 1134 3383964
Exposure via body fluid 55.33 38.09 10 751 428 3384670
Skin exfoliation 53.93 38.09 17 744 8020 3377078
Drug-induced liver injury 52.41 38.09 15 746 5098 3380000
Arthralgia 50.53 38.09 29 732 60832 3324266
Vein rupture 50.48 38.09 7 754 50 3385048
No adverse event 46.60 38.09 10 751 1040 3384058
Lip dry 43.31 38.09 9 752 802 3384296
Nausea 40.91 38.09 34 727 129611 3255487
Headache 39.56 38.09 29 732 91951 3293147
Liver function test abnormal 38.78 38.09 15 746 12886 3372212

Pharmacologic Action:

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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)

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DiseaseRelationSNOMED_IDDOID
Severe Recalcitrant Psoriasis indication
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Depressive disorder contraindication 35489007 DOID:2848
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
Lichen planus off-label use 4776004 DOID:9201
Keratosis follicularis off-label use 48611009 DOID:2734
Lamellar ichthyosis off-label use 205550003 DOID:1699
Ichthyosiform erythroderma off-label use 268282005 DOID:1699
Primary cutaneous T-cell lymphoma off-label use 400122007

Acid dissociation constants calculated using MoKa v3.0.0

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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:

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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:

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IDSource
DB00459 DRUGBANK_ID
4021061 VUID
N0000148524 NUI
C0050559 UMLSCUI
7598 IUPHAR_LIGAND_ID
D02754 KEGG_DRUG
4021061 VANDF
N0000007192 NDFRT
N0000148524 NDFRT
16818 RXNORM
108914001 SNOMEDCT_US
386938006 SNOMEDCT_US
4128 MMSL
d03836 MMSL
117161 MMSL
004121 NDDF
CHEMBL1131 ChEMBL_ID
5284513 PUBCHEM_CID
BK59Y5A02O UNII
69427-46-9 SECONDARY_CAS_RN
5530 INN_ID
D017255 MESH_DESCRIPTOR_UI
CHEBI:50173 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 0145-3817 CAPSULE 17.50 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 0591-2263 CAPSULE 10 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0591-2264 CAPSULE 17.50 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0591-2265 CAPSULE 22.50 mg ORAL ANDA 16 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0591-2266 CAPSULE 25 mg ORAL ANDA 16 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 12064-006 CAPSULE 10 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 12064-007 CAPSULE 17.50 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 12064-008 CAPSULE 25 mg ORAL Approved Drug Product Manufactured Under Contract 1 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