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Mls003373964

HCID 3877
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
134678-17-4
Standard SMILES
Nc1ccn(C2CSC(CO)O2)c(=O)n1
InChIKey
JTEGQNOMFQHVDC-UHFFFAOYSA-N
Molecular formula
C8H11N3O3S
Average molar mass
229.26 g/mol
Monoisotopic mass
229.05211239

Overview

See also: Dolutegravir sodium; lamivudine (annotation moved to); Lamivudine; tenofovir disoproxil fumarate (annotation moved to); 2',3'-Dideoxy-3'-thiacytidine (annotation moved to) ... View More ...

Names & identifiers

Preferred name
Mls003373964
IUPAC
4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
English name
Lamivudine
Molecular formula
C8H11N3O3S
Molecular weight
229.26

Names & synonyms

141434-39-1MLS003373964DTXSID10274412RefChem:357360DTXCID402258914-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-oneLamivudine Impurity B4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-oneCHEMBL1412'-deoxy-3'-thiacytidineNSC6207534-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
Show more names
3TC4-AMino-1-[(2R,5S)-2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyriMidinoneEpivirLaMivudine-13C-d2Zefix3¢L-SddCZeffix,3¢Hepitec
REF DUPLLamivudine Impurity 53cis-BCH-1894-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-onecid_60825SCHEMBL465678Lamivudine (3TC, BCH-189)HMS3393D21

Database identifiers

CAS
134678-17-4、141434-39-1

Properties

Computed structural properties

XLogP
-0.9
Topological polar surface area
113 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
15
Formal charge
0
Complexity
331

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

Melting point
177 °C · 177 °C
alpha
21 · D21 -135° (c = 0.38 in methanol)
Boiling point
475.4 · 475.4±55.0 °C(Predicted)
Density
1.73 · 1.73±0.1 g/cm3(Predicted)
refractive index
-142 ° · -142 ° (C=1, MeOH)
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
10 mg/mL, · water: soluble10mg/mL, clear
form
powder
pka
13.83 · 13.83±0.10(Predicted)
color
white to beige
Water Solubility
70 g/L · 70g/L(temperature not stated)
Merck
14 · 14,5352

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
UW7361333
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29349990
risk_code
63-36/37/38
Signal word
Warning
Symbol(GHS)
GHS08
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H361
Hazard Classifications
Repr. 2
Precautionary statements
P280
Hazardous Substances Data
134678-17-4(Hazardous Substances Data)

Chemistry & industry

Applications · 3 items

DescriptionLamivudine is a new generation orally active nucleoside analog launched in the U.S.A. for use in combination with zidovudine (AZT) as a first-line therapy for patients with HIV infection. Lamivudine is rapidly converted to phosphorylated metabolites in the body which act as inhibitors and chain terminators of HIV reverse transcriptase (RT), the enzyme required for the replication of the HIV genome. Lamivudine has similar inhibitory potency to RT as AZT but is 10 times less toxic and is active against AZT-resistant strains of HIV.

HistoryLamivudine[134678-17-4] is produced by GlaxoSmithKline LLC. In the early 1990s, it was used by some countries in Europe and North America to treat AIDS. In the mid-1990s, medical experts found that it had an inhibitory effect on the DNA of hepatitis B virus. In 1998, the US Food and Drug Administration (FDA) first approved it as a treatment drug for hepatitis B. In 1999, the China Food and Drug Administration approved this drug as a hepatitis B treatment drug, with the Chinese trade name "Heputin".

UsesLamivudine (Epivir-HBV) is in a class of medications called nucleoside reverse transcriptase inhibitors (NRTIs). It works by decreasing the amount of HIV and hepatitis B in the blood. It is used to treat hepatitis B infection. It is also used along with other medications to treat human immunodeficiency virus (HIV) infection in adults and children 3 months of age and older.

Upstream & downstream products

Upstream raw materials

Silica gelLead tetraacetateSilicon tetrahydrideChloroethaneSodium borohydrideSodium periodateBromideTetrabutylammonium Fluoride

Related reactions

2 records
New reaction record
HRID 2150589 reaction equation
HRID 2150589As productTraining data from https://doi.org/10.1039/C8SC04228D (4/10)
HRID 2340739 reaction equation
HRID 2340739As productTraining data from https://doi.org/10.1039/C8SC04228D (10/10)

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
3877
DTXSID
DTXSID10274412
Nikkaji
J762.340B
BCS Class
1 · 1,3
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
Major Application
pharmaceutical (small molecule)
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
InChIKey
JTEGQNOMFQHVDC-NKWVEPMBSA-N
SMILES
NC1=NC(=O)N(C=C1)[C@@H]2CS[C@H](CO)O2
Toxicology and Carcinogenesis
3 · Toxicology and Carcinogenesis Studies of Mixtures of 3'-Azido-3'-Deoxythymidine (AZT), Lamivudine (3TC), Nevirapine (NVP), and Nelfinavir Mesylate (NFV) (CASRNs 30516-87-1, 134678-17-4, 129618-40-2, 159989-65-8) in B6C3F1 Mice (Transplacental Exposure Studies)
CAS DataBase Reference
134678 · 134678-17-4(CAS DataBase Reference)
FDA UNII
2 T8Q726O95 · 2T8Q726O95
NCI Dictionary of Cancer Terms
lamivudine
NCI Drug Dictionary
Epivir
ATC code
5 AF05 · J05AF05
EPA Substance Registry System
2 · 2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- (134678-17-4)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Protein binding
36 % · <36%
Excreted unchanged in urine
70 % · 70%
Volume of distribution
1.3 · 1.3(L/kg)
Biological half-life
5 · 5-7 / 20
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
361 · H361
Precautionary statements
280 · P280
Risk Statements
63 · 63-36/37/38
Safety Statements
26 · 26-36
RIDADR
1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany
3 · 3
RTECS
7361333 · UW7361333
HS Code
29349990 · 29349990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 · Repr. 2
Hazardous Substances Data
134678 · 134678-17-4(Hazardous Substances Data)
Praseodymium(III) nitrate hexahydrate
Hexamethyldisilazane
Bromoacetaldehyde diethyl acetal
Chlorotrimethylsilane
Cytosine
Thiobenzoic acid
p-Toluenesulfonic acid
Potassium tert-butoxide

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
上海德默医药科技有限公司400-021-7337 2355568890 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
VDM Biochemicals0330-2528181 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
海门慧聚药业有限公司0086-15189180296 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
武汉海正工贸发展有限公司027-8866 0053/88660577/88660578
上海源叶生物科技有限公司18916372613 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
西安康培基生物科技有限公司86-029-85456576 · [email protected]
上海特伯化学科技有限公司+86-21-60341587 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
Shanghai Witofly Chemical Co.,Ltd[email protected]
越林试剂021-62960152 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
深圳市石金谷科技有限公司(0086)755-61930359 (0086)18038192047 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
潍坊鲁泽新材料有限公司0536-7971999 17176128999 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]

Additional notes

DefinitionChEBI: Lamivudine is a monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase.