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Also known as: Lamivudine + zidovudine, 165456-81-5, 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione, Lamivudine; zidovudine, Zidovudine / lamivudine, Lamivudine / zidovudine

Molecular Formula

C₁₈H₂₄N₈O₇S

Molecular Weight

496.5 g/mol

InChI Key

LHCOVOKZWQYODM-CPEOKENHSA-N

1 2D Structure

Lamivudine, Zidovudine Drug Combination

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

2.1.2 InChI

InChI=1S/C10H13N5O4.C8H11N3O3S/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8;9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h3,6-8,16H,2,4H2,1H3,(H,12,17,18);1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,8+;6-,7+/m00/s1

2.1.3 InChI Key

LHCOVOKZWQYODM-CPEOKENHSA-N

2.1.4 Canonical SMILES

CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-].C1C(OC(S1)CO)N2C=CC(=NC2=O)N

2.1.5 Isomeric SMILES

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-].C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Combivir

2. Lamivudine, Zidovudine Drug Combination

2.2.2 Depositor-Supplied Synonyms

1. Lamivudine + Zidovudine

2. 165456-81-5

3. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

4. Lamivudine; Zidovudine

5. Zidovudine / Lamivudine

6. Lamivudine / Zidovudine

7. Lamivudine, Zidovudine Drug Combination

8. 3tc / Zdv

9. Combivir(tm)

10. Lamivudine Mixture With Zidovudine

11. Zidovudine Mixture With Lamivudine

12. Epivir & Retrovir

13. 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one; 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

14. Mixture Of Lamivudine And Zidovudine

15. Lamivudine & Zidovudine

16. 3tc & Zdv

17. Azt & 3tc & Sst

18. (-)-3tc & Azt

19. .beta.-l-(-)-2',3'-dideoxy-3'-thiacytidine & 3'-azido-3'-deoxythymidine

20. .beta.-l-(-)-2',3'-dideoxy-3'-thiacytidine & 3'-azido-3'-deoxythymidine & Sho-saiko-to

21. Thymidine, 3'-azido-3'-deoxy-, Mixt. With 4-amino-1-((2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1h)-pyrimidinone

2.3 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₄N₈O₇S
Molecular Weight	496.5 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	496.14886631 g/mol
Monoisotopic Mass	496.14886631 g/mol
Topological Polar Surface Area	207 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	815
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Lamivudine and zidovudine
Drug Label	COMBIVIR: COMBIVIR Tablets are combination tablets containing lamivudine and zidovudine. Lamivudine (EPIVIR) and zidovudine (RETROVIR, azidothymidine, AZT, or ZDV) are synthetic nucleoside analogues with activity against HIV-1.COMBIVIR Tablets are fo...
Active Ingredient	Lamivudine and zidovudine; Lamivudine; zidovudine
Dosage Form	Tablet
Route	oral; Oral
Strength	150mg; 300mg
Market Status	Tentative Approval; Prescription
Company	Mylan Pharms; Hetero Labs Ltd V; Aurobindo Pharma; Lupin; Teva Pharms; Strides Arcolab

2 of 4
Drug Name	Lamivudine; zidovudine
Active Ingredient	efavirenz; Lamivudine; zidovudine
Dosage Form	Tablet, for suspension; Tablet
Route	oral; oral suspension
Strength	60mg; 30mg; 150mg; 600mg; 300mg
Market Status	Tentative Approval
Company	Macleods Pharma; Hetero Drugs; Aurobindo; Mylan Labs; Aurobindo Pharma; Cipla; Pharmacare; Matrix Labs; Emcure Pharma

3 of 4
Drug Name	Lamivudine and zidovudine
Drug Label	COMBIVIR: COMBIVIR Tablets are combination tablets containing lamivudine and zidovudine. Lamivudine (EPIVIR) and zidovudine (RETROVIR, azidothymidine, AZT, or ZDV) are synthetic nucleoside analogues with activity against HIV-1.COMBIVIR Tablets are fo...
Active Ingredient	Lamivudine and zidovudine; Lamivudine; zidovudine
Dosage Form	Tablet
Route	oral; Oral
Strength	150mg; 300mg
Market Status	Tentative Approval; Prescription
Company	Mylan Pharms; Hetero Labs Ltd V; Aurobindo Pharma; Lupin; Teva Pharms; Strides Arcolab

4 of 4
Drug Name	Lamivudine; zidovudine
Active Ingredient	efavirenz; Lamivudine; zidovudine
Dosage Form	Tablet, for suspension; Tablet
Route	oral; oral suspension
Strength	60mg; 30mg; 150mg; 600mg; 300mg
Market Status	Tentative Approval
Company	Macleods Pharma; Hetero Drugs; Aurobindo; Mylan Labs; Aurobindo Pharma; Cipla; Pharmacare; Matrix Labs; Emcure Pharma

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]

FDF Dossiers