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
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
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.83 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
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
Psoriasis 729.35 19.87 311 6594 78293 46600864
Skin exfoliation 93.24 19.87 59 6846 32879 46646278
Skin haemorrhage 91.53 19.87 34 6871 5857 46673300
Psoriatic arthropathy 90.29 19.87 60 6845 36319 46642838
Pruritus 72.68 19.87 129 6776 242223 46436934
Drug ineffective 68.54 19.87 237 6668 677601 46001556
Cutaneous T-cell lymphoma 67.60 19.87 19 6886 1344 46677813
Pregnancy 58.39 19.87 41 6864 27096 46652061
Dry skin 57.48 19.87 48 6857 40968 46638189
Skin plaque 56.71 19.87 24 6881 5811 46673346
Infected dermal cyst 55.25 19.87 13 6892 451 46678706
Pustular psoriasis 54.49 19.87 21 6884 3996 46675161
Rash pustular 52.75 19.87 24 6881 6905 46672252
Erythema 50.61 19.87 82 6823 142738 46536419
Rhesus antigen positive 47.08 19.87 9 6896 111 46679046
Drug exposure before pregnancy 46.77 19.87 12 6893 599 46678558
Wrong technique in device usage process 44.55 19.87 15 6890 1938 46677219
Erythrodermic psoriasis 42.31 19.87 12 6893 877 46678280
Skin fissures 41.42 19.87 21 6884 7659 46671498
Squamous cell carcinoma 38.15 19.87 20 6885 7816 46671341
Burning sensation 37.12 19.87 39 6866 44372 46634785
Guttate psoriasis 36.82 19.87 9 6896 368 46678789
Pregnancy of partner 35.69 19.87 6 6899 33 46679124
Skin lesion 34.82 19.87 30 6875 26683 46652474
Weaning failure 32.97 19.87 8 6897 317 46678840
Blood immunoglobulin M decreased 31.16 19.87 9 6896 702 46678455
Skin atrophy 29.93 19.87 14 6891 4286 46674871
Immunoglobulins decreased 29.61 19.87 9 6896 837 46678320
Type IIb hyperlipidaemia 29.37 19.87 5 6900 30 46679127
Blood albumin increased 29.20 19.87 9 6896 877 46678280
Lipids increased 28.06 19.87 9 6896 999 46678158
Abortion induced 28.06 19.87 18 6887 10242 46668915
Lip dry 27.63 19.87 12 6893 3092 46676065
Ichthyosis 27.30 19.87 5 6900 48 46679109
Onychalgia 27.24 19.87 8 6897 661 46678496
Sunburn 26.65 19.87 11 6894 2501 46676656
Exposure via body fluid 25.01 19.87 7 6898 487 46678670
Tanning 24.66 19.87 5 6900 85 46679072
Injection site bruising 24.07 19.87 28 6877 35608 46643549
Increased bronchial secretion 23.91 19.87 9 6896 1605 46677552
Inappropriate schedule of product administration 23.89 19.87 38 6867 64975 46614182
Rickets 23.79 19.87 4 6901 22 46679135
Blood immunoglobulin G decreased 22.63 19.87 9 6896 1859 46677298
Death 22.16 19.87 11 6894 335537 46343620
Mean cell haemoglobin increased 22.06 19.87 9 6896 1987 46677170
Exposure during pregnancy 21.91 19.87 49 6856 108163 46570994
Cellulitis 21.71 19.87 38 6867 70250 46608907
Keratoacanthoma 21.63 19.87 6 6899 404 46678753
Toxicity to various agents 21.34 19.87 3 6902 211763 46467394
Psoriasis area severity index increased 21.03 19.87 4 6901 48 46679109
Mastitis 20.83 19.87 9 6896 2289 46676868
Maternal exposure before pregnancy 20.57 19.87 11 6894 4470 46674687
Blister 20.56 19.87 29 6876 44602 46634555
Toxic goitre 20.16 19.87 3 6902 6 46679151
Serum ferritin decreased 20.16 19.87 8 6897 1644 46677513

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
Psoriasis 724.72 19.96 278 5324 42228 29904648
Vein rupture 199.20 19.96 41 5561 589 29946287
Drug ineffective 143.63 19.96 239 5363 340148 29606728
Skin plaque 131.72 19.96 42 5560 3620 29943256
Venous injury 111.54 19.96 22 5580 251 29946625
Injection site haemorrhage 100.44 19.96 42 5560 7813 29939063
Injection site papule 85.14 19.96 18 5584 296 29946580
Erythrodermic psoriasis 84.03 19.96 21 5581 741 29946135
Injection site swelling 83.14 19.96 38 5564 8742 29938134
Cutaneous T-cell lymphoma 72.36 19.96 21 5581 1314 29945562
Pityriasis rubra pilaris 69.05 19.96 12 5590 63 29946813
Skin erosion 58.49 19.96 19 5583 1734 29945142
Granuloma annulare 57.93 19.96 11 5591 101 29946775
Squamous cell carcinoma 57.27 19.96 31 5571 10219 29936657
Inappropriate schedule of product administration 56.78 19.96 52 5550 39676 29907200
Dermatitis exfoliative generalised 53.31 19.96 20 5582 2795 29944081
Squamous cell carcinoma of skin 52.19 19.96 28 5574 9067 29937809
Pain in extremity 49.41 19.96 80 5522 110141 29836735
Myalgia 46.30 19.96 64 5538 76603 29870273
Pustular psoriasis 39.86 19.96 14 5588 1621 29945255
Hypercholesterolaemia 39.75 19.96 22 5580 7570 29939306
Hyperkeratosis 39.73 19.96 17 5585 3340 29943536
Muscular weakness 39.72 19.96 54 5548 63591 29883285
Skin exfoliation 38.40 19.96 33 5569 23139 29923737
Dermatitis exfoliative 37.38 19.96 21 5581 7435 29939441
Keratoacanthoma 36.38 19.96 10 5592 513 29946363
Induration 35.70 19.96 11 5591 845 29946031
Basal cell carcinoma 35.34 19.96 27 5575 16041 29930835
Malignant melanoma stage I 34.22 19.96 7 5595 97 29946779
Psoriatic arthropathy 33.60 19.96 26 5576 15735 29931141
Neuroendocrine tumour of the lung metastatic 33.52 19.96 7 5595 108 29946768
Insomnia 32.95 19.96 61 5541 93275 29853601
Myasthenia gravis 31.65 19.96 14 5588 2978 29943898
Therapeutic product effect incomplete 31.27 19.96 35 5567 33799 29913077
Macule 31.10 19.96 10 5592 883 29945993
Retinal disorder 30.10 19.96 10 5592 979 29945897
Skin injury 29.96 19.96 10 5592 993 29945883
Erythema 29.07 19.96 52 5550 77399 29869477
Pruritus 28.47 19.96 66 5536 118138 29828738
Decreased immune responsiveness 27.59 19.96 10 5592 1268 29945608
Pain of skin 25.73 19.96 13 5589 3720 29943156
Hepatic cirrhosis 22.94 19.96 21 5581 15978 29930898
Sticky skin 22.75 19.96 3 5599 0 29946876
Cutaneous symptom 22.61 19.96 6 5596 269 29946607
Type 2 diabetes mellitus 21.75 19.96 19 5583 13603 29933273
Death 20.56 19.96 22 5580 357261 29589615
Hepatic fibrosis 20.47 19.96 11 5591 3569 29943307
Drug intolerance 20.40 19.96 33 5569 45258 29901618
Skin lesion 20.36 19.96 21 5581 18473 29928403
Superficial spreading melanoma stage unspecified 20.21 19.96 5 5597 169 29946707
Skin disorder 20.18 19.96 17 5585 11591 29935285

Pharmacologic Action:

SourceCodeDescription
ATC D05BB02 DERMATOLOGICALS
ANTIPSORIATICS
ANTIPSORIATICS FOR SYSTEMIC USE
Retinoids for treatment of psoriasis
FDA CS M0018962 Retinoids
FDA EPC N0000175607 Retinoid
MeSH PA D003879 Dermatologic Agents
MeSH PA D007641 Keratolytic Agents
CHEBI has role CHEBI:50176 desquamating agent

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
LCH760E9T7 UNII
4021061 VUID
N0000148524 NUI
D02754 KEGG_DRUG
69427-46-9 SECONDARY_CAS_RN
C0050559 UMLSCUI
CHEBI:50173 CHEBI
CHEMBL1131 ChEMBL_ID
5284513 PUBCHEM_CID
DB00459 DRUGBANK_ID
D017255 MESH_DESCRIPTOR_UI
5530 INN_ID
7598 IUPHAR_LIGAND_ID
16818 RXNORM
11379 MMSL
117161 MMSL
4128 MMSL
d03836 MMSL
004121 NDDF
108914001 SNOMEDCT_US
386938006 SNOMEDCT_US
4021061 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1135 CAPSULE 10 mg ORAL ANDA 24 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1136 CAPSULE 25 mg ORAL ANDA 24 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0093-1138 CAPSULE 17.50 mg ORAL ANDA 24 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 27 sections
SORIATANE HUMAN PRESCRIPTION DRUG LABEL 1 0145-0091 CAPSULE 25 mg ORAL NDA 27 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0378-7020 CAPSULE 10 mg ORAL ANDA 28 sections
Acitretin HUMAN PRESCRIPTION DRUG LABEL 1 0378-7023 CAPSULE 25 mg ORAL ANDA 28 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-086 CAPSULE 10 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-087 CAPSULE 17.50 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42291-088 CAPSULE 25 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-080 CAPSULE 10 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-081 CAPSULE 17.50 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 42794-083 CAPSULE 25 mg ORAL ANDA 25 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 66993-894 CAPSULE 10 mg ORAL NDA authorized generic 16 sections
ACITRETIN HUMAN PRESCRIPTION DRUG LABEL 1 66993-896 CAPSULE 25 mg ORAL NDA authorized generic 16 sections