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levonorgestrel 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
steroids, progestogens	1572	797-63-7

Description:

Molecule	Description
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 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

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

Status: OFP

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

Drug dosage:

Dose	Unit	Route
1.50	mg	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	94 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	9.40 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	52 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
CL (Clearance)	1.80 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	1.50 L/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.03 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
fu (Fraction unbound in plasma)	0.03 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
April 16, 1968	FDA	WYETH PHARMS
July 2, 2018	PMDA	Nobelpharma Co., Ltd.

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Device expulsion	125769.89	23.99	26185	131179	8737	63322921
Device dislocation	39315.79	23.99	9681	147683	16024	63315634
Genital haemorrhage	20358.42	23.99	4495	152869	2837	63328821
Uterine perforation	15528.32	23.99	3571	153793	3392	63328266
Pregnancy with contraceptive device	14071.41	23.99	3067	154297	1627	63330031
Complication of device insertion	11135.57	23.99	2775	154589	4789	63326869
Procedural pain	10699.66	23.99	3374	153990	18195	63313463
Abdominal pain lower	9735.51	23.99	3277	154087	22401	63309257
Embedded device	7798.69	23.99	1794	155570	1689	63329969
Pelvic pain	6911.75	23.99	2166	155198	11353	63320305

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Penile pain	3082.64	714.68	342	186	1221	34955182

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Device expulsion	95440.64	29.63	18307	104224	7554	79614303
Device dislocation	29197.68	29.63	6959	115572	19011	79602846
Genital haemorrhage	16657.42	29.63	3408	119123	2847	79619010
Uterine perforation	14334.57	29.63	3014	119517	3289	79618568
Pregnancy with contraceptive device	11135.13	29.63	2229	120302	1425	79620432
Complication of device insertion	9787.60	29.63	2207	120324	4143	79617714
Procedural pain	9556.38	29.63	2813	119718	20271	79601586
Abdominal pain lower	8131.06	29.63	2680	119851	29102	79592755
Embedded device	6586.78	29.63	1420	121111	1899	79619958
Pelvic pain	6140.16	29.63	1768	120763	11613	79610244

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
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	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	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
CHEBI has role	CHEBI:49323	contraceptive drugs

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID
Contraception	indication	13197004
Postmenopausal osteoporosis	indication	102447009
Menopausal flushing	indication	198436008
Dysmenorrhea	indication	266599000
Postcoital contraception	indication	268463003
Menorrhagia	indication	386692008
Controlled ovarian stimulation	indication	732970000
Female hypogonadism syndrome	off-label use	16041008
Polycystic ovaries	off-label use	69878008
Acne vulgaris	off-label use	88616000

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.02MG,0.15MG;0.025MG,0.15MG;0.03MG,0.15MG;0.01MG,N/A	QUARTETTE	TEVA BRANDED PHARM	N204061	March 28, 2013	RX	TABLET	ORAL	8450299	Oct. 7, 2025	PREVENTION OF PREGNANCY
0.02MG,0.1MG;0.01MG,N/A	LOSEASONIQUE	TEVA BRANDED PHARM	N022262	Oct. 24, 2008	RX	TABLET	ORAL	7615545	June 15, 2023	PREVENTION OF PREGNANCY
0.02MG,0.1MG;0.01MG,N/A	LOSEASONIQUE	TEVA BRANDED PHARM	N022262	Oct. 24, 2008	RX	TABLET	ORAL	7855190	Dec. 5, 2028	PREVENTION OF PREGNANCY
0.02MG;0.1MG	BALCOLTRA	AVION PHARMS	N208612	Jan. 9, 2018	RX	TABLET	ORAL	7838042	June 1, 2027	ADMINISTRATION OF FERROUS BISGLYCINATE TABLETS
0.03MG,0.01MG;0.15MG,N/A	SEASONIQUE	TEVA BRANDED PHARM	N021840	May 25, 2006	RX	TABLET	ORAL	7615545	June 15, 2023	PREVENTION OF PREGNANCY
0.03MG,0.01MG;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
0.03MG,0.01MG;0.15MG,N/A	SEASONIQUE	TEVA BRANDED PHARM	N021840	May 25, 2006	RX	TABLET	ORAL	7855190	Dec. 5, 2028	PREVENTION OF PREGNANCY
13.5MG	SKYLA	BAYER HLTHCARE	N203159	Jan. 9, 2013	RX	INTRAUTERINE DEVICE	INTRAUTERINE	10561524	Sept. 16, 2029	A METHOD OF POSITIONING AN INTRAUTERINE SYSTEM (IUS) BY DETERMINING A DEPTH OF THE UTERUS, HOLDING AN INSERTER HANDLE WITH ONE HAND, INSERTING THE IUS INTO THE UTERUS, AND RETRACTING A SLIDER ON THE HANDLE TO RELEASE THE IUS INTO THE UTERUS
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	10561524	Sept. 16, 2029	A METHOD OF POSITIONING AN INTRAUTERINE SYSTEM (IUS) BY DETERMINING A DEPTH OF THE UTERUS, HOLDING AN INSERTER HANDLE WITH ONE HAND, INSERTING THE IUS INTO THE UTERUS, AND RETRACTING A SLIDER ON THE HANDLE TO RELEASE THE IUS INTO THE UTERUS

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.02MG;0.1MG	TYBLUME	EXELTIS USA INC	N209405	March 30, 2020	RX	TABLET	ORAL	March 30, 2023	NEW DOSAGE FORM
0.03MG/24HR;0.12MG/24HR	TWIRLA	AGILE	N204017	Feb. 14, 2020	RX	SYSTEM	TRANSDERMAL	Feb. 14, 2023	NEW PRODUCT
52MG	MIRENA	BAYER HLTHCARE	N021225	Dec. 6, 2000	RX	INTRAUTERINE DEVICE	INTRAUTERINE	Aug. 20, 2023	DOSING REGIMEN EXTENDING THE CONTRACEPTION USE FROM 5 YEARS TO UP TO 6 YEARS
52MG	LILETTA	MEDICINES360	N206229	Feb. 26, 2015	RX	INTRAUTERINE DEVICE	INTRAUTERINE	June 29, 2026	TREATMENT OF HEAVY MENSTRUAL BLEEDING FOR UP TO 5 YEARS IN PATIENTS WHO CHOOSE INTRAUTERINE CONTRACEPTION AS THEIR METHOD OF CONTRACEPTION

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Progesterone receptor	Nuclear hormone receptor	P06401	PRGR_HUMAN	AGONIST	ED50	12.80	WOMBAT-PK	CHEMBL
Glucocorticoid receptor	Nuclear hormone receptor	P04150	GCR_HUMAN		Ki	7.17	DRUG MATRIX
Estrogen receptor	Nuclear hormone receptor	P03372	ESR1_HUMAN				WOMBAT-PK
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	6.23	DRUG MATRIX
Sex hormone-binding globulin	Secreted	P04278	SHBG_HUMAN		Kd	8.91	CHEMBL
Androgen receptor	Transcription factor		ANDR_RAT		Ki	8.37	DRUG MATRIX
Progesterone receptor	Transcription factor		Q690N0_BOVIN		Ki	9.34	DRUG MATRIX

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External reference:

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ID	Source
NOG	PDB_CHEM_ID
001303	NDDF
001304	NDDF
001325	NDDF
109032009	SNOMEDCT_US
126106007	SNOMEDCT_US
126109000	SNOMEDCT_US
13109	PUBCHEM_CID
180470	MMSL
2157	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Amethyst	HUMAN PRESCRIPTION DRUG LABEL	2	0480-3472	TABLET	90 ug	ORAL	ANDA	24 sections
Amethyst	HUMAN PRESCRIPTION DRUG LABEL	2	0480-3472	TABLET	90 ug	ORAL	ANDA	24 sections
EContra EZ	HUMAN OTC DRUG LABEL	1	50102-111	TABLET	1.50 mg	ORAL	ANDA	9 sections
EContra One-Step	Human OTC Drug Label	1	50102-211	TABLET	1.50 mg	ORAL	ANDA	14 sections
EContra One-Step	Human OTC Drug Label	1	50102-211	TABLET	1.50 mg	ORAL	ANDA	14 sections
Emergency Contraceptive	HUMAN OTC DRUG LABEL	1	0536-1391	TABLET	1.50 mg	ORAL	ANDA	13 sections
Kyleena	HUMAN PRESCRIPTION DRUG LABEL	1	50419-424	INTRAUTERINE DEVICE	19.50 mg	INTRAUTERINE	NDA	29 sections
Kyleena	HUMAN PRESCRIPTION DRUG LABEL	1	50419-424	INTRAUTERINE DEVICE	19.50 mg	INTRAUTERINE	NDA	29 sections
Levonorgestrel	HUMAN OTC DRUG LABEL	1	0536-1142	TABLET	1.50 mg	ORAL	ANDA	14 sections
Levonorgestrel	HUMAN PRESCRIPTION DRUG LABEL	1	40032-620	TABLET	1.50 mg	ORAL	ANDA	24 sections

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