LAMIVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H11N3O3S
Molecular Weight	229.256
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2CS[C@H](CO)O2

InChI

InChIKey=JTEGQNOMFQHVDC-NKWVEPMBSA-N

InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C8H11N3O3S
Molecular Weight	229.256
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Lamivudine is a reverse transcriptase inhibitor used alone or in combination with other classes of anti-human immunodeficiency virus (HIV) drugs in the treatment of HIV infection. This molecule has two stereo-centers, thus giving rise to four stereoisomers: (+/-)-cis-lamivudine and (+/-)-trans-lamivudine. The latter is considered to be impurity of the pharmaceutically active isomer, (-)-cis-lamivudine.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70	Inhibitor 8,504		2.0 nM [IC50]
DNA polymerase/reverse transcriptase 10	Inhibitor 8,504		3.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2,596
HIV-1 infection 156	Primary	Approved 8,583	EPIVIR
Chronic hepatitis B 16	Primary	Approved 8,583	EPIVIR

C_max

Value	Dose	Co-administered	Analyte	Population
1.4 μg/mL	150 mg 2 times / day multiple, oral		LAMIVUDINE plasma	Homo sapiens
3.3 μg/mL	300 mg single, oral		LAMIVUDINE blood	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
5.53 μg × h/mL	150 mg 2 times / day multiple, oral		LAMIVUDINE plasma	Homo sapiens
12.4 μg × h/mL	300 mg single, oral		LAMIVUDINE blood	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.9 h	300 mg single, oral		LAMIVUDINE blood	Homo sapiens

Doses

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Dose	Population	Adverse events
100 mg 1 times / day multiple, oral	unhealthy, 14.6	Other AEs: Malaise and fatigue, Ear, nose and throat infection...
10 mg/kg 2 times / day multiple, oral Highest studied dose	unhealthy, 37 years (range: 23-63 years)	Other AEs: Diarrhea, Abdominal discomfort...
4 mg/kg 2 times / day multiple, oral Highest studied dose	unhealthy, 7.6	Other AEs: Malaise and fatigue, Cough...
150 mg 1 times / day multiple, oral Recommended	unhealthy	Other AEs: Headache, Malaise and fatigue...

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AEs

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AE	Significance	Dose	Population
Ear, nose and throat infection	17%	100 mg 1 times / day multiple, oral	unhealthy, 14.6
Headache	17%	100 mg 1 times / day multiple, oral	unhealthy, 14.6
Malaise and fatigue	25%	100 mg 1 times / day multiple, oral	unhealthy, 14.6
Cough	8%	100 mg 1 times / day multiple, oral	unhealthy, 14.6
Ear, nose and throat infection	8%	100 mg 1 times / day multiple, oral	unhealthy, 14.6

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1,079 OATP1B3 961 MATE2 267 OCT3 159 BCRP 910 P-gp 1,741 OCT1 620 OCT2 779	MATE1 182 MATE2 98 OCT1 393 OCT2 434 P-gp 2,052 BCRP 697 CYP 303

Drug as perpetrator

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Target	Modality	Activity
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no
CYP3A4 2,633	inhibitor 4,027	no
MATE2 267	inhibitor 4,027	no
OATP1B1 1,095	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
CYP 303	substrate 4,014	not signifiicant
BCRP 697	substrate 4,014	yes
MATE1 182	substrate 4,014	yes
MATE2 98	substrate 4,014	yes
OCT1 393	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63577	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63577
ChemicalBook	CB1290608	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1290608
eMolecules	1987423	https://www.emolecules.com/cgi-bin/more?vid=1987423
eMolecules	2726078	https://www.emolecules.com/cgi-bin/more?vid=2726078
eMolecules	31588897	https://www.emolecules.com/cgi-bin/more?vid=31588897

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PubMed

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Title	Date	PubMed
Anti-HIV-1 activities of 1,3-dioxolane guanine and 2,6-diaminopurine dioxolane.	1999 Apr-May	10432704
Susceptibility of lamivudine-resistant hepatitis B virus to other reverse transcriptase inhibitors.	1999 Jun	10377169
Inhibition of human immunodeficiency virus type 1 replication in acutely and chronically infected cells by EM2487, a novel substance produced by a Streptomyces species.	1999 Oct	10508005
Pretherapy alanine transaminase level as a determinant for hepatitis B e antigen seroconversion during lamivudine therapy in patients with chronic hepatitis B. Asian Hepatitis Lamivudine Trial Group.	1999 Sep	10462384
Additional interferon alpha for lamivudine resistant hepatitis B infection after liver transplantation: a preliminary report.	2000 Apr 27	10836394

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Patents

Sample Use Guides

In Vivo Use Guide

Adults: 300 mg daily, administered as either 150 mg twice daily or 300 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

The antiviral activity of lamivudine against HIV-1 was assessed in a number of cell lines including monocytes and fresh human peripheral blood lymphocytes (PBMCs) using standard susceptibility assays. EC50 values were in the range of 0.003 to 15 microM (1 microM = 0.23 mcg per mL).

Substance Class	Chemical
Record UNII	2T8Q726O95
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

LAMIVUDINE

Official Name

English

DELSTRIGO COMPONENT LAMIVUDINE

Preferred Name

English

TEMIXYS COMPONENT LAMIVUDINE

Common Name

English

EPIVIR

Brand Name

English

LAMIVUDINE [EP MONOGRAPH]

Common Name

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175462

Antivirals for treatment of HIV infections, combinations

WHO-VATC

QJ05AR04

Antivirals for treatment of HIV infections, combinations

WHO-ATC

J05AR05

Antivirals for treatment of HIV infections, combinations

WHO-VATC

QJ05AR02

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

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Code System

Code

Type

Description

SMS_ID

100000085444

PRIMARY

INN

6908

PRIMARY

RXCUI

68244

PRIMARY

RxNorm

CHEBI

63577

PRIMARY

CAS

134678-17-4

PRIMARY

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Related Record

Type

Details


					PEM7E7C913

LAMIVUDINE METHANOL SOLVATE

SOLVATE->ANHYDROUS

Amount:


					PEM7E7C913

LAMIVUDINE METHANOL SOLVATE

SALT/SOLVATE -> PARENT

Amount:


					2T8Q726O95

LAMIVUDINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)


					2T8Q726O95

LAMIVUDINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [97.5 to 102] WEIGHT PERCENT (limits)


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

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Related Record

Type

Details


					RM8Y5KG43V

LAMIVUDINE TRIPHOSPHATE

METABOLITE ACTIVE -> PARENT

Amount:


					6IRT7BIB8R

LAMIVUDINE SULFOXIDE, (S)-

METABOLITE -> PARENT

Qualification:

URINE

Amount:

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					60KQZ0388Y

Troxacitabine

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP

Amount:


					SGC57V0D26

5-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-1,3-OXATHIOLANE-2-CARBOXYLIC ACID, CIS-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.3] PERCENT PEAK AREA (limits)


					8J337D1HZY

Cytosine

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP

Amount:


					3SN4QFF34D

LAMIVUDINE SULFOXIDE, (R)-

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP

Amount:


					6IRT7BIB8R

LAMIVUDINE SULFOXIDE, (S)-

IMPURITY -> PARENT

Amount:

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Related Record

Type

Details


					2T8Q726O95

LAMIVUDINE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	1.3 Liters/Kilogram [0.9 to 1.7] (average)

Biological Half-life	PHARMACOKINETIC	12.5 hours [10 to 15] (average)	Intercellular PHARMACOKINETIC 12.5 hours [11 to 15] (average) Elimination PHARMACOKINETIC 6 hours [5 to 7] (average) For adults; Increased with renal impairment. Elimination PHARMACOKINETIC 2 hours [1.4 to 2.6] (average) Children 4 mo. to 14 yr.

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator