levonorgestrel indications/contra

Stem definitionDrug idCAS RN
steroids, progestogens 1572 797-63-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • levonorgestrel
  • 18-Methylnorethindrone
  • D-Norgestrel
  • dexnorgestrel
  • norgestrel
A synthetic progestational hormone with actions similar to those of PROGESTERONE and about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.
  • Molecular weight: 312.45
  • Formula: C21H28O2
  • CLOGP: 3.32
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 37.30
  • ALOGS: -4.73
  • ROTB: 1

Drug dosage:

DoseUnitRoute
1.50 mg O

Approvals:

DateAgencyCompanyOrphan
April 16, 1968 FDA WYETH PHARMS

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
Device expulsion 79997.72 121.46 14401 21891 1792 3347775
Device dislocation 22185.92 121.46 4423 31869 2793 3346774
Uterine perforation 14280.21 121.46 2616 33676 51 3349516
Genital haemorrhage 9932.04 121.46 1859 34433 247 3349320
Pregnancy with contraceptive device 9888.47 121.46 1856 34436 278 3349289
Complication associated with device 8340.00 121.46 1961 34331 4677 3344890
Procedural pain 7834.97 121.46 1628 34664 1499 3348068
Abdominal pain lower 7688.84 121.46 1701 34591 2685 3346882
Vaginal haemorrhage 7574.51 121.46 1784 34508 4283 3345284
Injury 6789.93 121.46 1786 34506 7711 3341856
Pelvic pain 5765.35 121.46 1240 35052 1550 3348017
Device difficult to use 5421.37 121.46 1288 35004 3225 3346342
Abdominal pain 4751.38 121.46 2008 34284 44217 3305350
Pain 4212.80 121.46 2110 34182 69447 3280120
Uterine rupture 4139.26 121.46 773 35519 79 3349488
Emotional distress 4051.85 121.46 1094 35198 5266 3344301
Device issue 4044.41 121.46 1093 35199 5283 3344284
Complication of device insertion 3486.01 121.46 736 35556 771 3348796
Embedded device 3424.74 121.46 643 35649 85 3349482
Menorrhagia 3344.28 121.46 865 35427 3390 3346177
Amenorrhoea 2945.94 121.46 720 35572 2097 3347470
Medical device discomfort 2751.75 121.46 534 35758 184 3349383
Complication of device removal 2426.05 121.46 497 35795 380 3349187
Device breakage 2268.82 121.46 616 35676 3016 3346551
Ectopic pregnancy with contraceptive device 2252.20 121.46 416 35876 14 3349553
Anxiety 2241.17 121.46 1142 35150 38487 3311080
Depression 2081.02 121.46 1088 35204 38682 3310885
Dyspareunia 2076.05 121.46 420 35872 276 3349291
Ovarian cyst 1619.27 121.46 414 35878 1520 3348047
Medical device pain 1602.51 121.46 311 35981 106 3349461

Pharmacologic Action:

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SourceCodeDescription
ATC G03AC03 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Progestogens
ATC G03AD01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
Emergency contraceptives
ATC G03AA06 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 G03AA07 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 G03AB03 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 G03FA10 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, fixed combinations
ATC G03FA11 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, fixed combinations
ATC G03FB01 GENITO URINARY SYSTEM AND SEX HORMONES
SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
PROGESTOGENS AND ESTROGENS IN COMBINATION
Progestogens and estrogens, sequential preparations
ATC G03FB09 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 PE N0000175830 Inhibit Ovum Fertilization
FDA Chemical/Ingredient N0000011301 Progesterone Congeners
FDA EPC N0000175602 Progestin
FDA EPC N0000175832 Progestin-containing Intrauterine Device
CHEBI has role CHEBI:49323 contraceptive drug
CHEBI has role CHEBI:49326 synthetic oral contraceptive
CHEBI has role CHEBI:49324 female contraceptive drug
MeSH PA D003270 Contraceptive Agents
MeSH PA D003271 Contraceptive Agents, Female
MeSH PA D003276 Contraceptives, Oral
MeSH PA D003280 Contraceptives, Oral, Synthetic
MeSH PA D012102 Reproductive Control Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Contraception indication 13197004
Postmenopausal osteoporosis indication 102447009
Menopausal flushing indication 198436008
Postcoital contraception indication 268463003
Menorrhagia indication 386692008
Heart valve disorder contraindication 368009 DOID:4079
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Congenital heart disease contraindication 13213009 DOID:1682
Hypercholesterolemia contraindication 13644009
Amenorrhea contraindication 14302001 DOID:13938
Jaundice contraindication 18165001
Myocardial infarction contraindication 22298006 DOID:5844
Puerperal endometritis contraindication 22399000
Diplopia contraindication 24982008
Retinal hemorrhage contraindication 28998008
Streptococcal septicemia contraindication 29577008
Vaginitis contraindication 30800001 DOID:2170
Ectopic pregnancy contraindication 34801009 DOID:0060329
Depressive disorder contraindication 35489007 DOID:2848
Chloasma contraindication 36209000
Inflammation of cervix contraindication 37610005 DOID:2568
Migraine contraindication 37796009 DOID:6364
Congenital uterine anomaly contraindication 37849005
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 DOID:1727
Humoral hypercalcemia of malignancy contraindication 47709007
Chronic heart failure contraindication 48447003
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 DOID:13603
Thrombophlebitis contraindication 64156001 DOID:3875
Blood coagulation disorder contraindication 64779008 DOID:1247
Intermenstrual bleeding - irregular contraindication 64996003
Miscarriage with sepsis contraindication 67465009
Diabetes mellitus contraindication 73211009 DOID:9351
Cyst of ovary contraindication 79883001
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Human immunodeficiency virus infection contraindication 86406008 DOID:526
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:2527
Leukemia, disease contraindication 93143009 DOID:1240
Malignant neoplasm of liver contraindication 93870000 DOID:3571
Uterine leiomyoma contraindication 95315005 DOID:13223
Neoplasm of endometrium contraindication 123844007 DOID:1380
Neoplasm of liver contraindication 126851005 DOID:3571
Deep venous thrombosis contraindication 128053003
Seizure disorder contraindication 128613002 DOID:1826
Bed-ridden contraindication 160685001
Liver function tests abnormal contraindication 166603001
Mammography abnormal contraindication 168750009
Angina pectoris contraindication 194828000
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007 DOID:6713
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Cholestasis of pregnancy contraindication 235888006
Uterine perforation by intrauterine contraceptive device contraindication 236738001
Endometrial carcinoma contraindication 254878006 DOID:2871
Chorea contraindication 271700006
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Abnormal uterine bleeding unrelated to menstrual cycle contraindication 312984006
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 DOID:13268
Bacterial vaginosis contraindication 419760006 DOID:3385
Optic disc edema contraindication 423341008 DOID:10175
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
Severe Headache Disorder contraindication
Intrauterine Device Insertion with Acute Vaginitis contraindication
Inflammatory Disease of Female Pelvic Organs contraindication
Uterine Scarring contraindication
Major Surgery with Prolonged Post-Operative Immobilization contraindication
Female hypogonadism syndrome off-label use 16041008
Polycystic ovaries off-label use 69878008 DOID:11612
Acne vulgaris off-label use 88616000
Endometriosis off-label use 129103003 DOID:289
Dysmenorrhea off-label use 266599000

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.09MG **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** LYBREL WYETH PHARMS INC N021864 May 22, 2007 DISCN TABLET ORAL 6500814 Sept. 3, 2018 PREVENTION OF PREGNANCY
0.25MG PREVEN EMERGENCY CONTRACEPTIVE KIT TEVA BRANDED PHARM N020946 Sept. 1, 1998 DISCN TABLET ORAL 6156742 Dec. 5, 2020 KIT ADAPTED AND DESIGNED TO PROVIDE BOTH DATA ON THE CURRENT REPRODUCTIVE STATUS OF A PATIENT AND CONTRACEPTION FOR THOSE WHO ARE NOT PREGNANT, BUT RECENTLY ENGAGED IN UNPROTECTED SEX
0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7615545 June 15, 2023 PREVENTION OF PREGNANCY
0.1MG,N/A LOSEASONIQUE TEVA BRANDED PHARM N022262 Oct. 24, 2008 RX TABLET ORAL 7615545 June 15, 2023 PREVENTION OF PREGNANCY
0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7320969 Jan. 30, 2024 PREVENTION OF PREGNANCY IN WOMEN WHO ELECT TO USE ORAL CONTRACEPTIVES AS A METHOD OF CONTRACEPTION
None QUARTETTE TEVA BRANDED PHARM N204061 March 28, 2013 RX TABLET ORAL 8450299 Oct. 7, 2025 PREVENTION OF PREGNANCY
0.15MG,N/A SEASONIQUE TEVA BRANDED PHARM N021840 May 25, 2006 RX TABLET ORAL 7855190 Dec. 5, 2028 PREVENTION OF PREGNANCY
0.1MG,N/A LOSEASONIQUE TEVA BRANDED PHARM N022262 Oct. 24, 2008 RX TABLET ORAL 7855190 Dec. 5, 2028 PREVENTION OF PREGNANCY
52MG MIRENA BAYER HLTHCARE N021225 Dec. 6, 2000 RX INTRAUTERINE DEVICE INTRAUTERINE 9615965 Sept. 16, 2029 A METHOD OF POSITIONING AN INTRAUTERINE SYSTEM BY HOLDING AN INSERTER HANDLE WITH ONE HAND, ADVANCING THE INSERTER THROUGH THE CERVIX AND INTO THE UTERUS, AND RETRACTING A SLIDER ON THE HANDLE TO RELEASE THE INTRAUTERINE SYSTEM
13.5MG SKYLA BAYER HLTHCARE N203159 Jan. 9, 2013 RX INTRAUTERINE DEVICE INTRAUTERINE 9615965 Sept. 16, 2029 A METHOD OF POSITIONING AN INTRAUTERINE SYSTEM BY HOLDING AN INSERTER HANDLE WITH ONE HAND, ADVANCING THE INSERTER THROUGH THE CERVIX AND INTO THE UTERUS, AND RETRACTING A SLIDER ON THE HANDLE TO RELEASE THE INTRAUTERINE SYSTEM
19.5MG KYLEENA BAYER HLTHCARE N208224 Sept. 16, 2016 RX INTRAUTERINE DEVICE INTRAUTERINE 9615965 Sept. 16, 2029 A METHOD OF POSITIONING AN INTRAUTERINE SYSTEM BY HOLDING AN INSERTER HANDLE WITH ONE HAND, ADVANCING THE INSERTER THROUGH THE CERVIX AND INTO THE UTERUS, AND RETRACTING A SLIDER ON THE HANDLE TO RELEASE THE INTRAUTERINE SYSTEM

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
52MG LILETTA MEDICINES360 N206229 Feb. 26, 2015 RX INTRAUTERINE DEVICE INTRAUTERINE Feb. 26, 2018 NEW PRODUCT
19.5MG KYLEENA BAYER HLTHCARE N208224 Sept. 16, 2016 RX INTRAUTERINE DEVICE INTRAUTERINE Sept. 16, 2019 NEW PRODUCT

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Progesterone receptor Nuclear hormone receptor AGONIST ED50 12.80 WOMBAT-PK CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 6.23 DRUG MATRIX
Glucocorticoid receptor Nuclear hormone receptor Ki 7.17 DRUG MATRIX
Sex hormone-binding globulin Secreted Kd 8.91 CHEMBL
Estrogen receptor Nuclear hormone receptor WOMBAT-PK
Androgen receptor Transcription factor Ki 8.37 DRUG MATRIX
Progesterone receptor Transcription factor Ki 9.34 DRUG MATRIX

External reference:

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IDSource
DB00367 DRUGBANK_ID
2881 IUPHAR_LIGAND_ID
4018027 VUID
N0000146370 NUI
C0023566 UMLSCUI
D00950 KEGG_DRUG
3J8Q1747Z2 UNII
2157 INN_ID
6533-00-2 SECONDARY_CAS_RN
6373 RXNORM
126109000 SNOMEDCT_US
4974 MMSL
d00557 MMSL
109032009 SNOMEDCT_US
4018027 VANDF
N0000007395 NDFRT
N0000146370 NDFRT
180470 MMSL
001304 NDDF
CHEMBL1389 ChEMBL_ID
13109 PUBCHEM_CID
CHEMBL2107797 ChEMBL_ID
D009644 MESH_DESCRIPTOR_UI
D016912 MESH_DESCRIPTOR_UI
DB09389 DRUGBANK_ID
CHEBI:6443 CHEBI
NOG PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
LILETTA HUMAN PRESCRIPTION DRUG LABEL 1 0023-5858 INTRAUTERINE DEVICE 52 mg INTRAUTERINE NDA 18 sections
Camrese HUMAN PRESCRIPTION DRUG LABEL 3 0093-3134 KIT 0.15 mg None NDA authorized generic 19 sections
Rivelsa HUMAN PRESCRIPTION DRUG LABEL 7 0093-6031 KIT 0.15 mg None NDA authorized generic 19 sections
Rivelsa HUMAN PRESCRIPTION DRUG LABEL 7 0093-6031 KIT 0.15 mg None NDA authorized generic 19 sections
Rivelsa HUMAN PRESCRIPTION DRUG LABEL 7 0093-6031 KIT 0.15 mg None NDA authorized generic 19 sections
camrese Lo HUMAN PRESCRIPTION DRUG LABEL 3 0093-6148 KIT 0.10 mg None NDA authorized generic 19 sections
Option 2 HUMAN OTC DRUG LABEL 1 0113-2003 TABLET 1.50 mg ORAL ANDA 13 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-6550 KIT 0.15 mg None ANDA 13 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7281 KIT 0.15 mg None ANDA 19 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 3 0378-7284 KIT 0.10 mg None ANDA 17 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 3 0378-7285 KIT 0.15 mg None ANDA 18 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7287 KIT 0.10 mg None ANDA 13 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 2 0378-7298 KIT 0.10 mg None ANDA 14 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 7 0378-7316 KIT 0.15 mg None ANDA 19 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 7 0378-7316 KIT 0.15 mg None ANDA 19 sections
LEVONORGESTREL AND ETHINYL ESTRADIOL AND ETHINYL ESTRADIOL HUMAN PRESCRIPTION DRUG LABEL 7 0378-7316 KIT 0.15 mg None ANDA 19 sections
Lessina HUMAN PRESCRIPTION DRUG LABEL 2 0555-9014 KIT 0.10 mg None ANDA 15 sections
Portia HUMAN PRESCRIPTION DRUG LABEL 2 0555-9020 KIT 0.15 mg None ANDA 14 sections
Aviane HUMAN PRESCRIPTION DRUG LABEL 2 0555-9045 KIT 0.10 mg None ANDA 12 sections
Enpresse HUMAN PRESCRIPTION DRUG LABEL 6 0555-9047 KIT 0.13 mg None ANDA 13 sections
Enpresse HUMAN PRESCRIPTION DRUG LABEL 6 0555-9047 KIT 0.05 mg None ANDA 13 sections
Enpresse HUMAN PRESCRIPTION DRUG LABEL 6 0555-9047 KIT 0.08 mg None ANDA 13 sections
Cryselle HUMAN PRESCRIPTION DRUG LABEL 2 0555-9049 KIT 0.30 mg None ANDA 12 sections
Jolessa HUMAN PRESCRIPTION DRUG LABEL 2 0555-9123 KIT 0.15 mg None NDA authorized generic 19 sections
Myzilra HUMAN PRESCRIPTION DRUG LABEL 6 0603-7625 KIT 0.08 mg None ANDA 14 sections
Myzilra HUMAN PRESCRIPTION DRUG LABEL 6 0603-7625 KIT 0.13 mg None ANDA 14 sections
Myzilra HUMAN PRESCRIPTION DRUG LABEL 6 0603-7625 KIT 0.05 mg None ANDA 14 sections
Orsythia HUMAN PRESCRIPTION DRUG LABEL 2 0603-7634 KIT 0.10 mg ORAL ANDA 13 sections
Vienva TM HUMAN PRESCRIPTION DRUG LABEL 2 0781-5575 KIT 0.10 mg None ANDA 13 sections
ALTAVERA HUMAN PRESCRIPTION DRUG LABEL 2 0781-5583 KIT 0.15 mg None ANDA 8 sections