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

Stem definition	Drug id	CAS RN
uridine derivatives used as antiviral agents and as antineoplastics	1539	134678-17-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: lamivudine virolam zeffix	A reverse transcriptase inhibitor and ZALCITABINE analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat HIV disease. Molecular weight: 229.25 Formula: C8H11N3O3S CLOGP: -1.46 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 88.15 ALOGS: -1.92 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

lamivudine
virolam
zeffix

A reverse transcriptase inhibitor and ZALCITABINE analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat HIV disease.

Molecular weight: 229.25
Formula: C8H11N3O3S
CLOGP: -1.46
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 88.15
ALOGS: -1.92
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.30	g	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	9.10 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	86 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
S (Water solubility)	70 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	67 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	4.80 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	21.81 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	1.30 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.94 %	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
Aug. 8, 1996	EMA	VIIV HLTHCARE
Jan. 14, 2020	PMDA	ViiV Healthcare K.K.
Nov. 17, 1995	FDA	VIIV HLTHCARE

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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
Exposure during pregnancy	2121.32	16.80	1142	27840	154405	63305635
Abortion spontaneous	1380.09	16.80	587	28395	46608	63413432
Virologic failure	1328.05	16.80	277	28705	1585	63458455
Viral mutation identified	1277.81	16.80	267	28715	1543	63458497
Drug resistance	1103.34	16.80	409	28573	22524	63437516
Stillbirth	1059.81	16.80	296	28686	6454	63453586
Foetal exposure during pregnancy	915.10	16.80	392	28590	31570	63428470
Pathogen resistance	879.79	16.80	253	28729	6145	63453895
Immune reconstitution inflammatory syndrome	811.67	16.80	235	28747	5849	63454191
Abortion induced	687.23	16.80	234	28748	10008	63450032

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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
Viral mutation identified	1896.03	12.37	497	47825	2457	34906152
Virologic failure	1640.19	12.37	459	47863	3021	34905588
Immune reconstitution inflammatory syndrome	1590.79	12.37	557	47765	8202	34900407
Pathogen resistance	1409.72	12.37	520	47802	8962	34899647
Drug resistance	968.69	12.37	542	47780	25385	34883224
Lipodystrophy acquired	841.73	12.37	272	48050	3072	34905537
Depression	772.34	12.37	803	47519	96295	34812314
Foetal exposure during pregnancy	753.38	12.37	532	47790	37569	34871040
Drug interaction	752.24	12.37	1212	47110	224734	34683875
Hepatitis B	624.76	12.37	254	48068	5729	34902880

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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
Immune reconstitution inflammatory syndrome	2422.54	12.93	743	60920	13098	79669627
Viral mutation identified	2382.31	12.93	561	61102	3297	79679428
Virologic failure	2377.48	12.93	569	61094	3622	79679103
Pathogen resistance	1800.44	12.93	598	61065	13744	79668981
Drug resistance	1691.38	12.93	767	60896	41446	79641279
Exposure during pregnancy	1100.85	12.93	782	60881	100350	79582375
Lipodystrophy acquired	1089.13	12.93	308	61355	4017	79678708
Abortion spontaneous	1058.95	12.93	497	61166	29010	79653715
Stillbirth	832.47	12.93	245	61418	3710	79679015
Hepatitis B reactivation	771.37	12.93	256	61407	5852	79676873

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FDA Adverse Event Reporting System (Pediatric)

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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
Neutropenia	37.65	36.60	22	638	195	88937

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Pharmacologic Action:

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Source	Code	Description
ATC	J05AF05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Nucleoside and nucleotide reverse transcriptase inhibitors
ATC	J05AR01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR04	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR11	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR12	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR13	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR16	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations

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

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Disease	Relation	SNOMED_ID	DOID
Chronic type B viral hepatitis	indication	61977001
Human immunodeficiency virus infection	indication	86406008	DOID:526
Prevention of Hepatitis B Reactivation in Immunocompromised Patients	off-label use
Prevention of HIV Infection after Exposure	off-label use
Toxic amblyopia	contraindication	965003
Myositis	contraindication	26889001	DOID:633
Hepatic failure	contraindication	59927004
Pancreatitis	contraindication	75694006	DOID:4989
Large liver	contraindication	80515008
Kidney disease	contraindication	90708001	DOID:557

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.95	acidic
pKa2	4.18	Basic

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
100MG;300MG;300MG	DELSTRIGO	MSD MERCK CO	N210807	Aug. 30, 2018	RX	TABLET	ORAL	8486975	Oct. 7, 2031	FOR THE TREATMENT OF HIV-1 INFECTION IN ADULT PATIENTS WITH NO PRIOR ANTIRETROVIRAL TREATMENT HISTORY
100MG;300MG;300MG	DELSTRIGO	MSD MERCK CO	N210807	Aug. 30, 2018	RX	TABLET	ORAL	8486975	Oct. 7, 2031	TREATMENT OF HIV-1 INFECTION IN ADULT PATIENTS AS A REPLACEMENT THERAPY IN VIROLOGICALLY SUPPRESSED ADULTS WITH NO HISTORY OF TREATMENT FAILURE AND NO KNOWN SUBSTITUTIONS ASSOCIATED WITH RESISTANCE TO THE INDIVIDUAL COMPONENTS OF DELSTRIGO
100MG;300MG;300MG	DELSTRIGO	MSD MERCK CO	N210807	Aug. 30, 2018	RX	TABLET	ORAL	8486975	Oct. 7, 2031	TREATMENT OF HIV-1 INFECTION IN PEDIATRIC PATIENTS WEIGHING AT LEAST 35KG WITH NO PRIOR ANTIRETROVIRAL TREATMENT HISTORY OR TO REPLACE THE CURRENT ANTIRETROVIRAL REGIMEN IN THOSE WHO ARE VIROLOGICALLY SUPPRESSED
150MG;EQ 300MG BASE	DUTREBIS	MERCK SHARP DOHME	N206510	Feb. 6, 2015	DISCN	TABLET	ORAL	7754731	March 11, 2029	TREATMENT OF HIV-1 INFECTION
EQ 50MG BASE;300MG	DOVATO	VIIV HLTHCARE	N211994	April 8, 2019	RX	TABLET	ORAL	11234985	Jan. 24, 2031	TREATMENT OF HIV INFECTION

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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
100MG;300MG;300MG	DELSTRIGO	MSD MERCK CO	N210807	Aug. 30, 2018	RX	TABLET	ORAL	Aug. 30, 2023	NEW CHEMICAL ENTITY
100MG;300MG;300MG	DELSTRIGO	MSD MERCK CO	N210807	Aug. 30, 2018	RX	TABLET	ORAL	Jan. 27, 2025	NEW PATIENT POPULATION
EQ 50MG BASE;300MG	DOVATO	VIIV HLTHCARE	N211994	April 8, 2019	RX	TABLET	ORAL	Aug. 6, 2023	TO REPLACE THE CURRENT ANTIRETROVIRAL REGIMEN IN THOSE WHO ARE VIROLOGICALLY SUPRESSED (HIV-1 RNA LESS THAN 50 COPIES PER ML) ON A STABLE ANTIRETROVIRAL REGIMEN WITH NO HISTORY OF TREATMENT FAILURE
EQ 600MG BASE;EQ 50MG BASE;300MG	TRIUMEQ	VIIV HLTHCARE	N205551	Aug. 22, 2014	RX	TABLET	ORAL	June 15, 2026	INFORMATION ADDED TO THE LABELING REGARDING THE RESULT OF STUDY 205860
EQ 600MG BASE;EQ 50MG BASE;300MG	TRIUMEQ	VIIV HLTHCARE	N205551	Aug. 22, 2014	RX	TABLET	ORAL	Dec. 15, 2026	PEDIATRIC EXCLUSIVITY
EQ 60MG BASE;EQ 5MG BASE;30MG	TRIUMEQ PD	VIIV HLTHCARE	N215413	March 30, 2022	RX	TABLET, FOR SUSPENSION	ORAL	June 15, 2026	NEW PATIENT POPULATION
EQ 60MG BASE;EQ 5MG BASE;30MG	TRIUMEQ PD	VIIV HLTHCARE	N215413	March 30, 2022	RX	TABLET, FOR SUSPENSION	ORAL	Dec. 15, 2026	PEDIATRIC EXCLUSIVITY

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Deoxycytidine kinase	Kinase	P27707	DCK_HUMAN				WOMBAT-PK
Protein P	Polyprotein		Q9IF40_HBV	INHIBITOR			CHEMBL	CHEMBL
Reverse transcriptase/RNaseH	Enzyme		Q72547_9HIV1	INHIBITOR	EC50	7.38	CHEMBL	CHEMBL
Capsid protein	Unclassified		Q03732_HBV		EC50	6.43	CHEMBL

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External reference:

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ID	Source
3TC	PDB_CHEM_ID
005079	NDDF
108698001	SNOMEDCT_US
12673	IUPHAR_LIGAND_ID
186277	MMSL
2T8Q726O95	UNII
386897000	SNOMEDCT_US
4020938	VUID
4020938	VANDF
4956	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Abacavir and Lamivudine	Human Prescription Drug Label	2	35573-402	TABLET, FILM COATED	300 mg	ORAL	ANDA	29 sections
Abacavir and Lamivudine	Human Prescription Drug Label	2	35573-430	TABLET, FILM COATED	300 mg	ORAL	ANDA	27 sections
Abacavir and Lamivudine	Human Prescription Drug Label	2	35573-430	TABLET, FILM COATED	300 mg	ORAL	ANDA	27 sections
Abacavir and Lamivudine	HUMAN PRESCRIPTION DRUG LABEL	2	42291-115	TABLET, FILM COATED	300 mg	ORAL	ANDA	28 sections
Combivir	HUMAN PRESCRIPTION DRUG LABEL	2	16590-061	TABLET, FILM COATED	150 mg	ORAL	NDA	16 sections
COMBIVIR	HUMAN PRESCRIPTION DRUG LABEL	2	21695-846	TABLET, FILM COATED	150 mg	ORAL	NDA	26 sections
DELSTRIGO	HUMAN PRESCRIPTION DRUG LABEL	3	0006-5007	TABLET, FILM COATED	300 mg	ORAL	NDA	32 sections
DELSTRIGO	HUMAN PRESCRIPTION DRUG LABEL	3	0006-5007	TABLET, FILM COATED	300 mg	ORAL	NDA	32 sections
EPIVIR	HUMAN PRESCRIPTION DRUG LABEL	1	21695-367	TABLET, FILM COATED	150 mg	ORAL	NDA	26 sections
EPIVIRHBV	HUMAN PRESCRIPTION DRUG LABEL	1	0173-0662	TABLET, FILM COATED	100 mg	ORAL	NDA	26 sections

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