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Also known as: 1377049-84-7, Gs-5816, Gs5816, Kcu0c7rs7z, Gs 5816, Methyl ((r)-2-((2s,4s)-2-(5-(2-((2s,5s)-1-((methoxycarbonyl)-l-valyl)-5-methylpyrrolidin-2-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate
Molecular Formula
C49H54N8O8
Molecular Weight
883.0  g/mol
InChI Key
FHCUMDQMBHQXKK-CDIODLITSA-N
FDA UNII
KCU0C7RS7Z

Velpatasvir
Velpatasvir is an orally available inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex, with potential activity against HCV genotypes 1-6. Although the exact mechanism of action of velpatasvir has not yet been completely determined, upon oral administration and intracellular uptake, it appears to bind to domain I of the NS5A protein. This inhibits the activity of the NS5A protein and results in the disruption of the viral RNA replication complex, blockage of viral HCV RNA production, and inhibition of viral replication. NS5A, a zinc-binding and proline-rich hydrophilic phosphoprotein, plays a crucial role in HCV RNA replication. HCV is a small, enveloped, single-stranded RNA virus belonging to the Flaviviridae family.
Velpatasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of velpatasvir is as a Breast Cancer Resistance Protein Inhibitor, and P-Glycoprotein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Organic Anion Transporting Polypeptide 2B1 Inhibitor.
1 2D Structure

Velpatasvir

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl N-[(1R)-2-[(2S,4S)-2-[5-[6-[(2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),5,9,11,14(19),15,17-nonaen-17-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
2.1.2 InChI
InChI=1S/C49H54N8O8/c1-26(2)41(54-48(60)63-5)47(59)57-27(3)12-17-38(57)45-51-36-16-14-30-20-35-33-15-13-31(19-32(33)25-65-40(35)21-34(30)43(36)53-45)37-22-50-44(52-37)39-18-28(24-62-4)23-56(39)46(58)42(55-49(61)64-6)29-10-8-7-9-11-29/h7-11,13-16,19-22,26-28,38-39,41-42H,12,17-18,23-25H2,1-6H3,(H,50,52)(H,51,53)(H,54,60)(H,55,61)/t27-,28-,38-,39-,41-,42+/m0/s1
2.1.3 InChI Key
FHCUMDQMBHQXKK-CDIODLITSA-N
2.1.4 Canonical SMILES
CC1CCC(N1C(=O)C(C(C)C)NC(=O)OC)C2=NC3=C(N2)C=CC4=CC5=C(C=C43)OCC6=C5C=CC(=C6)C7=CN=C(N7)C8CC(CN8C(=O)C(C9=CC=CC=C9)NC(=O)OC)COC
2.1.5 Isomeric SMILES
C[C@H]1CC[C@H](N1C(=O)[C@H](C(C)C)NC(=O)OC)C2=NC3=C(N2)C=CC4=CC5=C(C=C43)OCC6=C5C=CC(=C6)C7=CN=C(N7)[C@@H]8C[C@@H](CN8C(=O)[C@@H](C9=CC=CC=C9)NC(=O)OC)COC
2.2 Other Identifiers
2.2.1 UNII
KCU0C7RS7Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gs-5816

2.3.2 Depositor-Supplied Synonyms

1. 1377049-84-7

2. Gs-5816

3. Gs5816

4. Kcu0c7rs7z

5. Gs 5816

6. Methyl ((r)-2-((2s,4s)-2-(5-(2-((2s,5s)-1-((methoxycarbonyl)-l-valyl)-5-methylpyrrolidin-2-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

7. Methyl [(2s)-1-[(2s,5s)-2-[9-[2-[(2s,4s)-1-[(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl]-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

8. Methyl N-[(1r)-2-[(2s,4s)-2-[5-[6-[(2s,5s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),5,9,11,14(19),15,17-nonaen-17-yl]-1h-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

9. Unii-kcu0c7rs7z

10. Velpatasvir [usan:inn]

11. Verpatasvir

12. Methyl ((2s)-1-((2s,5s)-2-(9-(2-((2s,4s)-1-((2r)-2-((methoxycarbonyl)amino)-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1h-imidazol-5-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate

13. Methyl {(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

14. Velpatasvir [inn]

15. Velpatasvir(gs5816)

16. Velpatasvir [mi]

17. Velpatasvir [jan]

18. Velpatasvir; Gs-5816

19. Velpatasvir [usan]

20. Velpatasvir [who-dd]

21. Velpatasvir (jan/usan/inn)

22. Schembl8756902

23. Chembl3545062

24. Schembl19236068

25. Gtpl11269

26. Amy4211

27. Dtxsid70722565

28. Velpatasvir [orange Book]

29. Chebi:133009

30. Epclusa (sofosbuvir + Velpatasvir)

31. Vosevi Component Velpatasvir

32. Bcp13813

33. Epclusa Component Velpatasvir

34. Ex-a2320

35. Bdbm50521720

36. Mfcd28411371

37. S3724

38. Velpatasvir Component Of Vosevi

39. Zinc203686879

40. Ccg-270553

41. Cs-5977

42. Db11613

43. Velpatasvir Component Of Epclusa

44. Ncgc00522503-01

45. Ncgc00522503-02

46. Ac-28744

47. As-35237

48. Hy-12530

49. Ft-0700879

50. J3.631.686a

51. D10806

52. Gs-5816;gs5816;gs 5816

53. Vosevi (sofosbuvir + Velpatasvir + Voxilaprevi)

54. A886410

55. Q25018296

56. Carbamic Acid, N-[(1r)-2-[(2s,4s)-2-[5-[1,11-dihydro-2-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4,3:6,7]naphth[1,2-d]imidazol-9-yl]-1h-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinyl]-2-oxo-1-phenylethyl]-, Methyl Ester

57. Methyl {(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-4-yl}-1,11-dihydro[2]benzopyrano[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

58. Methyl N-[(1r)-2-[(2s,4s)-2-(5-{6-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.0?,??.0?,?.0??,??]henicosa-1,3,6,8,10,12,14,16,18-nonaen-17-yl}-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

59. Methyl N-[(1r)-2-[(2s,4s)-2-(5-{6-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.0?,?.01?,1?]henicosa-1,3,6,8,10,12,14,16,18-nonaen-17-yl}-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

60. Methyl{(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

2.4 Create Date
2012-11-30
3 Chemical and Physical Properties
Molecular Weight 883.0 g/mol
Molecular Formula C49H54N8O8
XLogP36.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count13
Exact Mass882.40646071 g/mol
Monoisotopic Mass882.40646071 g/mol
Topological Polar Surface Area193 Ų
Heavy Atom Count65
Formal Charge0
Complexity1690
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameEPCLUSA
Active IngredientSOFOSBUVIR; VELPATASVIR
CompanyGILEAD SCIENCES INC (Application Number: N208341. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9757406)

2 of 2  
Drug NameVOSEVI
Active IngredientSOFOSBUVIR; VELPATASVIR; VOXILAPREVIR
CompanyGILEAD SCIENCES INC (Application Number: N209195. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9296782, 9585906)

4.2 Drug Indication

Velpatasvir is used in combination therapy with other antiviral medications to treat chronic hepatitis C virus (HCV) infected patients with HCV genoptypes 1-6, and to treat HCV and HIV co-infected patients. Depending on the level of cirrhosis or decompensation, combination therapy can also include therapy with [DB00811]. When used in combination with [DB08934] as the combination product Epclusa, Velpatasvir is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5, or 6 infection without cirrhosis or with compensated cirrhosis, or in combination with [DB00811] if associated with decompensated cirrhosis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Velpatasvir is a small molecule direct-acting antiviral used in the treatment of hepatitis C in combination with sofosbuvir. Velpatasvir prevents viral replication by inhibiting non-structural protein 5A (NS5A). At a dose 5 times the recommended dose, velpatasvir does not prolong QTc interval to any clinically relevant extent.


5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
VELPATASVIR
5.3.2 FDA UNII
KCU0C7RS7Z
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Organic Anion Transporting Polypeptide 2B1 Inhibitors
5.4 Absorption, Distribution and Excretion

Absorption

Oral bioavailability of 25-30%.


Route of Elimination

94% excreted in feces with 77% as parent compound. 0.4% excreted in urine.


Volume of Distribution

1.4-1.6 L/kg.


Clearance

Estimated 0.12 L/h/kg [A19175.


5.5 Metabolism/Metabolites

Some metabolism by CYP2B6, CYP2C8, and CYP3A4.


5.6 Biological Half-Life

15h.


5.7 Mechanism of Action

Velpatasvir's mechanism of action is likely similar to other selective NS5A inhibitors which bind domain I of NS5A consisting of amino acids 33-202. NS5A inhibitors compete with RNA for binding at this site. It is also thought that NS5A inhibitors bind the target during its action in replication when the binding site is exposed. Inhibition of NS5A is also known to produce redistribution of the protein to lipid droplets. The exact role of NS5A in RNA replication is not yet understood although it is known to be an important component.


API Reference Price

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AMBEKAR MARG, WADALA","city":"MUMBAI, MAHARASHTRA","supplier":"ZHEJIANG CHEMICALS I & E CORP","supplierCountry":"CHINA","foreign_port":"#N\/A","customer":"FREDUN PHARMACEUTICALS LTD","customerCountry":"INDIA","quantity":"0.50","actualQuantity":"0.5","unit":"KGS","unitRateFc":"4095","totalValueFC":"2120.5","currency":"USD","unitRateINR":"315929.3","date":"06-Jan-2022","totalValueINR":"157964.63","totalValueInUsd":"2120.5","indian_port":"BOMBAY AIR","hs_no":"29349990","bill_no":"6980743","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"#N\/A","supplierAddress":"","customerAddress":"26, MANOJ INDUSTRIAL ESTATE, G.D. AMBEKAR MARG, WADALA"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1641407400,"product":"VELPATASVIR","address":"26, MANOJ INDUSTRIAL ESTATE, G.D. AMBEKAR MARG, WADALA","city":"MUMBAI, MAHARASHTRA","supplier":"ZHEJIANG CHEMICALS I & E CORP","supplierCountry":"CHINA","foreign_port":"#N\/A","customer":"FREDUN PHARMACEUTICALS LTD","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"4095","totalValueFC":"8482.1","currency":"USD","unitRateINR":"315929.3","date":"06-Jan-2022","totalValueINR":"631858.5","totalValueInUsd":"8482.1","indian_port":"BOMBAY AIR","hs_no":"29349990","bill_no":"6980743","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"#N\/A","supplierAddress":"","customerAddress":"26, MANOJ INDUSTRIAL ESTATE, G.D. AMBEKAR MARG, WADALA"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1659119400,"product":"VELPATASVIR BATCH NO.:RD-VLP-202202201 MFG DATE:FEB.20, 2022EXP DATE: FEB.20, 2024(AS PER ADVANCE LIC)","address":"A-202, 2ND FLOOR, MONDEAL SQUARE BLDG,VEJALPUR:OPP:KARANAVATI CLUB,","city":"S.G. HIGH WAY,AHMEDABAD, GUJARAT.","supplier":"CHANGZHOU PHARMACEUTICAL FACTORY","supplierCountry":"CHINA","foreign_port":"NA","customer":"MEDWISE OVERSEAS PRIVATE ","customerCountry":"INDIA","quantity":"1.40","actualQuantity":"1.4","unit":"KGS","unitRateFc":"4000","totalValueFC":"5701","currency":"USD","unitRateINR":"323800","date":"30-Jul-2022","totalValueINR":"453320","totalValueInUsd":"5701","indian_port":"AHMEDABAD AIR","hs_no":"29349990","bill_no":"9799958","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"A-202, 2ND FLOOR, MONDEAL SQUARE BLDG,VEJALPUR:OPP:KARANAVATI CLUB,"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1671042600,"product":"VELPATASVIR (CAS NO : 1377049-84-7)","address":"1017\/1018, CORPORATE AVENUE,,SONAW ALA ROAD,GOREGAON EAST,","city":"MUMBAI MAHARASHTRA,MAHARASHTRA","supplier":"ALARIS PHARMACEUTICALS PTE ","supplierCountry":"CHINA","foreign_port":"NA","customer":"BIOPHARMA","customerCountry":"INDIA","quantity":"7.00","actualQuantity":"7","unit":"KGS","unitRateFc":"4017","totalValueFC":"27980.4","currency":"USD","unitRateINR":"329394","date":"15-Dec-2022","totalValueINR":"2305758","totalValueInUsd":"27980.4","indian_port":"BOMBAY AIR","hs_no":"29349990","bill_no":"3760085","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"1017\/1018, CORPORATE AVENUE,,SONAW ALA ROAD,GOREGAON EAST,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1706293800,"product":"VELPATASVIR","address":"MEDREICH HOUSE, NO12\/8,","city":"SEVA NAGAR, BANGALORE, KARNATAKA","supplier":"ZHEJIANG Z-STAR PHARMA CO., LTD","supplierCountry":"CHINA","foreign_port":"HANGCHOW (HANGZHOU)","customer":"MEDREICH","customerCountry":"INDIA","quantity":"2.50","actualQuantity":"2.5","unit":"KGS","unitRateFc":"4650","totalValueFC":"11763.2","currency":"USD","unitRateINR":"391065","date":"27-Jan-2024","totalValueINR":"977662.5","totalValueInUsd":"11763.2","indian_port":"Bangalore Air","hs_no":"29349990","bill_no":"9855348","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HANGCHOW (HANGZHOU)","supplierAddress":"ROOM 1507, EAST NO.1, BUILDING,TENGDA CENRAL NO1800, DONGHAI ROADJIAOJIANG DIST, TAIZHOU CITY CHINA","customerAddress":"MEDREICH HOUSE, NO12\/8,"}]
01-Jan-2021
19-Sep-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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INTERMEDIATES SUPPLIERS

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01

PMC Isochem

France
Pharmtech & Ingredients
Not Confirmed
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  • EDQM
  • WHO-GMP

Virtual BoothPMC Isochem is your partner for smart CDMOs of Intermediates, APIs, & excipients & a catalog of Intermediates & Generic APIs.

CAS Number : 74761-42-5

End Use API : Velpatasvir

About The Company : PMC Isochem is a CDMO company acquired by PMC International in 2017. It manufactures cGMP intermediates, active pharmaceutical ingredients and functional excipi...

PMC Isochem

02

PMC Isochem

France
Pharmtech & Ingredients
Not Confirmed
arrow
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothPMC Isochem is your partner for smart CDMOs of Intermediates, APIs, & excipients & a catalog of Intermediates & Generic APIs.

CAS Number : 50890-96-5

End Use API : Velpatasvir

About The Company : PMC Isochem is a CDMO company acquired by PMC International in 2017. It manufactures cGMP intermediates, active pharmaceutical ingredients and functional excipi...

PMC Isochem

03

Pharmtech & Ingredients
Not Confirmed
arrow
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothCapital Farma, a leading European pharmaceutical company focusing on the development & distribution of niche APIs & Pharma Services.

CAS Number : 2935-35-5

End Use API : Velpatasvir

About The Company : Capital Farma offers a comprehensive range of pharmaceutical solutions. Our API offering includes active ingredients sourced exclusively from top European manuf...

Capital Farma

04

Pharmtech & Ingredients
Not Confirmed
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Pharmtech & Ingredients
Not Confirmed
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CAS Number : CAS-1335316-40-9

End Use API : Velpatasvir

About The Company : Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutic...

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05

Pharmtech & Ingredients
Not Confirmed
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Pharmtech & Ingredients
Not Confirmed
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CAS Number : CAS-1378391-43-5

End Use API : Velpatasvir

About The Company : Beijing Mesochem Technology Co. Ltd., which is located in the national economic and technological development area of Yizhuang, China, manufactures pharmaceutic...

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06

Pharmtech & Ingredients
Not Confirmed
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Pharmtech & Ingredients
Not Confirmed
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CAS Number : 1377049-84-7

End Use API : Velpatasvir

About The Company : Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-...

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07

Pharmtech & Ingredients
Not Confirmed
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Pharmtech & Ingredients
Not Confirmed
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CAS Number : 22009-38-7

End Use API : Velpatasvir

About The Company : Ningbo Chemgoo is a R&D-driven company with core technology of organic chemistry, dedicating in technology development and industrialization. We provide interme...

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08

Pharmtech & Ingredients
Not Confirmed
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Pharmtech & Ingredients
Not Confirmed
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CAS Number : 946525-30-0

End Use API : Velpatasvir

About The Company : Ningbo Chemgoo is a R&D-driven company with core technology of organic chemistry, dedicating in technology development and industrialization. We provide interme...

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