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

Stem definitionDrug idCAS RN
steroids, progestogens 818 54024-22-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • Org 2969
  • desogestrel
  • cerazette
A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents (ORAL CONTRACEPTIVES, COMBINED).
  • Molecular weight: 310.48
  • Formula: C22H30O
  • CLOGP: 5.50
  • LIPINSKI: 1
  • HAC: 1
  • HDO: 1
  • TPSA: 20.23
  • ALOGS: -5.01
  • ROTB: 1

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.32 mg/mL 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) 0.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 5 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 10, 1992 FDA ORGANON USA 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
Muscle injury 1477.33 24.81 609 36398 29157 53282902
Folliculitis 1473.60 24.81 619 36388 31090 53280969
Irritable bowel syndrome 1323.74 24.81 632 36375 43000 53269059
Lower respiratory tract infection 1266.57 24.81 786 36221 90195 53221864
Impaired healing 1075.01 24.81 625 36382 63580 53248479
Blister 1001.71 24.81 643 36364 78110 53233949
Sleep disorder due to general medical condition, insomnia type 964.92 24.81 425 36582 23924 53288135
Ill-defined disorder 931.25 24.81 520 36487 48924 53263135
Gastrointestinal disorder 893.13 24.81 630 36377 89374 53222685
Sinusitis 853.97 24.81 796 36211 167768 53144291
Stomatitis 848.55 24.81 632 36375 97526 53214533
Peripheral swelling 742.14 24.81 809 36198 205299 53106760
Therapeutic product effect decreased 667.74 24.81 610 36397 125045 53187014
Joint swelling 603.90 24.81 776 36231 233862 53078197
Pruritus 571.87 24.81 849 36158 292983 53019076
Infection 545.60 24.81 633 36374 171572 53140487
Nasopharyngitis 529.26 24.81 658 36349 191637 53120422
Weight increased 521.91 24.81 674 36333 203893 53108166
Swelling 500.51 24.81 638 36369 190467 53121592
Duodenal ulcer perforation 468.09 24.81 296 36711 34887 53277172
Hypersensitivity 466.68 24.81 648 36359 210017 53102042
Confusional state 464.35 24.81 620 36387 193601 53118458
Helicobacter infection 454.20 24.81 302 36705 38767 53273292
Muscle spasticity 369.40 24.81 200 36807 17638 53294421
Rash 330.45 24.81 858 36149 445333 52866726
Pericarditis 322.61 24.81 303 36704 64103 53247956
Anti-cyclic citrullinated peptide antibody positive 321.51 24.81 287 36720 56885 53255174
Contraindicated product administered 312.95 24.81 426 36581 135203 53176856
Night sweats 281.17 24.81 216 36791 34731 53277328
Contusion 269.36 24.81 357 36650 110375 53201684
Ear pain 266.71 24.81 196 36811 29477 53282582
Body temperature increased 264.47 24.81 203 36804 32596 53279463
Discomfort 248.02 24.81 318 36689 95154 53216905
Respiratory disorder 246.78 24.81 198 36809 33899 53278160
Hand deformity 228.87 24.81 288 36719 84561 53227498
Pyrexia 228.02 24.81 704 36303 402489 52909570
Death 220.27 24.81 6 37001 357226 52954833
Glossodynia 205.80 24.81 298 36709 99993 53212066
Synovitis 203.31 24.81 308 36699 107585 53204474
Pemphigus 196.04 24.81 297 36710 103734 53208325
Wound 187.75 24.81 272 36735 91285 53220774
Hepatic enzyme increased 180.47 24.81 318 36689 125877 53186182
Arthralgia 177.77 24.81 687 36320 439096 52872963
Pneumonia 177.30 24.81 34 36973 407135 52904924
Systemic lupus erythematosus 160.23 24.81 301 36706 125113 53186946
Fall 155.85 24.81 30 36977 358410 52953649
Sleep disorder 143.25 24.81 190 36817 58680 53253379
Pain 141.86 24.81 790 36217 587608 52724451
Arthropathy 138.46 24.81 304 36703 141149 53170910
Acute kidney injury 129.58 24.81 13 36994 253855 53058204
Infusion related reaction 129.35 24.81 314 36693 155643 53156416
Nausea 129.25 24.81 204 36803 755887 52556172
Toxicity to various agents 124.06 24.81 7 37000 219591 53092468
Anaemia 122.69 24.81 22 36985 276696 53035363
Urticaria 109.88 24.81 271 36736 135614 53176445
Hypotension 108.79 24.81 22 36985 254054 53058005
Insomnia 97.27 24.81 318 36689 186754 53125305
Malaise 96.47 24.81 65 36942 357552 52954507
Dyspnoea 94.73 24.81 712 36295 585520 52726539
Pregnancy on oral contraceptive 81.29 24.81 32 36975 1347 53310712
Drug hypersensitivity 80.22 24.81 42 36965 265200 53046859
Dehydration 75.42 24.81 13 36994 168397 53143662
Decreased appetite 74.49 24.81 28 36979 214946 53097113
Urinary tract infection 74.01 24.81 37 36970 239866 53072193
Abdominal discomfort 73.62 24.81 326 36681 220736 53091323
Weight decreased 72.83 24.81 36 36971 234912 53077147
Neutropenia 69.74 24.81 13 36994 159172 53152887
Oedema peripheral 68.61 24.81 17 36990 170770 53141289
Alopecia 67.86 24.81 332 36675 234251 53077808
Drug intolerance 67.62 24.81 302 36705 205191 53106868
Product dose omission issue 66.31 24.81 25 36982 191595 53120464
Sepsis 66.23 24.81 11 36996 146418 53165641
Atrial fibrillation 64.77 24.81 3 37004 111649 53200410
Renal failure 63.25 24.81 5 37002 118447 53193612
Hyponatraemia 62.74 24.81 3 37004 108604 53203455
Cough 62.37 24.81 52 36955 256841 53055218
Febrile neutropenia 60.29 24.81 3 37004 104933 53207126
Abdominal pain upper 58.19 24.81 249 36758 166042 53146017
Dizziness 57.27 24.81 107 36900 372152 52939907
White blood cell count decreased 57.08 24.81 9 36998 124466 53187593
Platelet count decreased 56.51 24.81 5 37002 108094 53203965
Pain in extremity 56.31 24.81 69 36938 284981 53027078
Blood pressure increased 54.47 24.81 15 36992 140464 53171595
Therapeutic product effect incomplete 51.55 24.81 3 37004 91781 53220278
Hypertension 50.67 24.81 49 36958 225382 53086677
Somnolence 50.02 24.81 27 36980 167707 53144352
Bronchitis 49.29 24.81 9 36998 111890 53200169
Respiratory failure 49.06 24.81 6 37001 100506 53211553
Constipation 48.33 24.81 40 36967 198372 53113687
Gait disturbance 48.20 24.81 25 36982 158817 53153242
Thrombocytopenia 46.49 24.81 19 36988 138708 53173351
Blood creatinine increased 45.53 24.81 3 37004 82659 53229400
Neuropathy peripheral 43.97 24.81 9 36998 103178 53208881
Pancytopenia 43.00 24.81 6 37001 90922 53221137
Overdose 42.71 24.81 11 36996 107725 53204334
Haemoglobin decreased 42.57 24.81 21 36986 137286 53174773
Injection site pain 42.31 24.81 13 36994 113378 53198681
Feeling abnormal 41.49 24.81 21 36986 135280 53176779
Fatigue 40.99 24.81 722 36285 729784 52582275
Condition aggravated 40.90 24.81 91 36916 297043 53015016
Renal impairment 40.60 24.81 5 37002 83313 53228746
Myalgia 40.51 24.81 21 36986 133470 53178589
Leukopenia 39.49 24.81 3 37004 73460 53238599
Maternal exposure during pregnancy 37.82 24.81 210 36797 155429 53156630
Faecal volume decreased 36.87 24.81 11 36996 196 53311863
Hypokalaemia 36.13 24.81 11 36996 96506 53215553
Cellulitis 35.97 24.81 5 37002 75984 53236075
Cerebrovascular accident 35.89 24.81 14 36993 105160 53206899
Cardiac failure 35.53 24.81 8 36999 85836 53226223
Pleural effusion 35.19 24.81 9 36998 88570 53223489
Herpes zoster 34.73 24.81 5 37002 74014 53238045
Blood glucose increased 34.55 24.81 6 37001 77355 53234704
Syncope 33.41 24.81 18 36989 111975 53200084
Tension 32.33 24.81 23 36984 3283 53308776
Septic shock 32.19 24.81 3 37004 62226 53249833
Gastrooesophageal reflux disease 31.71 24.81 9 36998 82654 53229405
Aspartate aminotransferase increased 30.69 24.81 10 36997 84019 53228040
Hospitalisation 30.65 24.81 6 37001 71006 53241053
Cardio-respiratory arrest 29.95 24.81 3 37004 58755 53253304
Erythema 29.91 24.81 39 36968 156930 53155129
Off label use 29.61 24.81 199 36808 472013 52840046
Upper respiratory tract infection 29.49 24.81 6 37001 69091 53242968
Coma 29.39 24.81 4 37003 61779 53250280
Arthritis 29.16 24.81 12 36995 87286 53224773
Asthma 29.04 24.81 20 36987 108952 53203107
Alanine aminotransferase increased 28.78 24.81 15 36992 95080 53216979
Loss of personal independence in daily activities 27.91 24.81 7 37000 69808 53242251
Hypoglycaemia 27.65 24.81 4 37003 59009 53253050
Tachycardia 27.35 24.81 21 36986 108191 53203868
Muscle spasms 27.24 24.81 32 36975 134763 53177296
Depressed level of consciousness 27.17 24.81 3 37004 54425 53257634
Chest pain 27.17 24.81 57 36950 190128 53121931
Chills 26.95 24.81 20 36987 104828 53207231
Cardiac arrest 26.59 24.81 16 36991 93651 53218408
Depression 26.03 24.81 55 36952 182997 53129062
Hypoaesthesia 25.38 24.81 33 36974 132962 53179097
Diarrhoea 24.96 24.81 296 36711 625250 52686809

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

Pharmacologic Action:

SourceCodeDescription
ATC G03AA09 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, fixed combinations
ATC G03AB05 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens and estrogens, sequential preparations
ATC G03AC09 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens
ATC G03FB10 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, sequential preparations
FDA CS M0447349 Progesterone Congeners
FDA EPC N0000175602 Progestin
CHEBI has role CHEBI:49323 contraceptive agent
CHEBI has role CHEBI:49326 synthetic oral contraceptives
CHEBI has role CHEBI:59826 progestins
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D000080066 Contraceptive Agents, Hormonal
MeSH PA D003278 Contraceptives, Oral, Hormonal
MeSH PA D003280 Contraceptives, Oral, Synthetic
MeSH PA D006728 Hormones
MeSH PA D011372 Progestins
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Contraception indication 13197004
Amenorrhea off-label use 14302001 DOID:13938
Female hypogonadism syndrome off-label use 16041008
Polycystic ovaries off-label use 69878008
Dysmenorrhea off-label use 266599000
Abnormal uterine bleeding unrelated to menstrual cycle off-label use 312984006
Menorrhagia off-label use 386692008
Heart valve disorder contraindication 368009 DOID:4079
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Depressive disorder contraindication 35489007
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Body fluid retention contraindication 43498006
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Hyperlipidemia contraindication 55822004 DOID:1168
Benign mammary dysplasia contraindication 57993004
Obstructive hyperbilirubinemia contraindication 59848001
Thrombophlebitis contraindication 64156001 DOID:3875
Intermenstrual bleeding - irregular contraindication 64996003
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Malignant neoplasm of liver contraindication 93870000 DOID:3571
Uterine leiomyoma contraindication 95315005 DOID:13223
Deep venous thrombosis contraindication 128053003
Endometriosis contraindication 129103003
Liver function tests abnormal contraindication 166603001
Mammography abnormal contraindication 168750009
Angina pectoris contraindication 194828000
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Cholestasis of pregnancy contraindication 235888006
Endometrial carcinoma contraindication 254878006 DOID:2871
Chorea contraindication 271700006
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Malignant tumor of cervix contraindication 363354003 DOID:4362
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Cardiovascular event risk contraindication 395112001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Porphyria contraindication 418470004
Family history of malignant neoplasm of breast contraindication 429740004
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002
Nonspecific Abnormal Papanicolaou Smear of Cervix contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.93 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
Progesterone receptor Nuclear hormone receptor AGONIST WOMBAT-PK CHEMBL
Sex hormone-binding globulin Secreted Kd 6.60 CHEMBL

External reference:

IDSource
4020568 VUID
N0000148270 NUI
D02367 KEGG_DRUG
C0057558 UMLSCUI
CHEBI:4453 CHEBI
CHEMBL1533 ChEMBL_ID
DB00304 DRUGBANK_ID
D017135 MESH_DESCRIPTOR_UI
40973 PUBCHEM_CID
7065 IUPHAR_LIGAND_ID
4384 INN_ID
81K9V7M3A3 UNII
22656 RXNORM
4549 MMSL
d03780 MMSL
003956 NDDF
116074007 SNOMEDCT_US
126108008 SNOMEDCT_US
4020568 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MERCILON HUMAN OTC DRUG LABEL 2 72689-0020 TABLET 0.15 mg ORAL unapproved drug other 7 sections