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    Chemistry

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    Also known as: 654671-78-0, Sitagliptin (phosphate), Mk-0431, Chembl393336, 494p4635i6, Mk0431
    Molecular Formula
    C16H18F6N5O5P
    Molecular Weight
    505.31  g/mol
    InChI Key
    IQFYVLUXQXSJJN-SBSPUUFOSA-N
    FDA UNII
    494P4635I6
    Sitagliptin Phosphate
    A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.
    1 2D Structure

    Sitagliptin Phosphate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric acid
    2.1.2 InChI
    InChI=1S/C16H15F6N5O.H3O4P/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;1-5(2,3)4/h4,6,9H,1-3,5,7,23H2;(H3,1,2,3,4)/t9-;/m1./s1
    2.1.3 InChI Key
    IQFYVLUXQXSJJN-SBSPUUFOSA-N
    2.1.4 Canonical SMILES
    C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
    2.1.5 Isomeric SMILES
    C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
    2.2 Other Identifiers
    2.2.1 UNII
    494P4635I6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 0431, Mk

    2. 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine

    3. Anhydrous, Sitagliptin Phosphate

    4. Januvia

    5. Mk 0431

    6. Mk-0431

    7. Mk0431

    8. Monohydrate, Sitagliptin Monophosphate

    9. Monohydrate, Sitagliptin Phosphate

    10. Monophosphate Monohydrate, Sitagliptin

    11. Phosphate Anhydrous, Sitagliptin

    12. Phosphate Monohydrate, Sitagliptin

    13. Phosphate, Sitagliptin

    14. Sitagliptin

    15. Sitagliptin Monophosphate Monohydrate

    16. Sitagliptin Phosphate Anhydrous

    17. Sitagliptin Phosphate Monohydrate

    2.3.2 Depositor-Supplied Synonyms

    1. 654671-78-0

    2. Sitagliptin (phosphate)

    3. Mk-0431

    4. Chembl393336

    5. 494p4635i6

    6. Mk0431

    7. (2r)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate Salt

    8. (3r)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric Acid

    9. (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate

    10. 1-butanone, 3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-, (3r)-, Phosphate (1:1)

    11. Sitagliptin Monophosphate

    12. Sitagliptin Phosphate Anhydrous

    13. (3r)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)-1-butanone; Phosphoric Acid

    14. Mk 0431

    15. Sr-05000001748

    16. Unii-494p4635i6

    17. (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate Salt

    18. Mk 431

    19. Mk-0431 Phosphate

    20. Schembl877069

    21. Dtxsid10215789

    22. Hy-13749a

    23. Mfcd09952339

    24. Akos015896098

    25. Sitagliptin Phosphate [who-dd]

    26. Ks-1214

    27. 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate

    28. Sitagliptin Monophosphate Anhydrous [mi]

    29. 671s780

    30. A835125

    31. Sr-05000001748-2

    32. Q27259224

    33. Sitagliptin Phosphate Anhydrous Component Of Janumet

    34. (3r)-3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone Phosphate

    35. (3r)-3-azanyl-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-[2,4,5-tris(fluoranyl)phenyl]butan-1-one; Phosphoric Acid

    36. 1,2,4-triazolo(4,3-a)pyrazine, 7-((3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8-tetrahydro-3-(trifluoromethyl)-, Phosphate (1:1)

    37. 1269630-53-6

    38. 7-((3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo(4,3-a)pyrazinemonophosphate

    39. 7-(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine Phosphate

    2.4 Create Date
    2006-04-29
    3 Chemical and Physical Properties
    Molecular Weight 505.31 g/mol
    Molecular Formula C16H18F6N5O5P
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count4
    Exact Mass505.09497466 g/mol
    Monoisotopic Mass505.09497466 g/mol
    Topological Polar Surface Area155 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity616
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameJanuvia
    PubMed HealthSitagliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelJANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 50mg base; eq 25mg base
    Market StatusPrescription
    CompanyMerck Sharp Dohme

    2 of 4  
    Drug NameSitagliptin phosphate
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    Routeoral; Oral
    Strengtheq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
    Market StatusTentative Approval
    CompanyMylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

    3 of 4  
    Drug NameJanuvia
    PubMed HealthSitagliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelJANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 50mg base; eq 25mg base
    Market StatusPrescription
    CompanyMerck Sharp Dohme

    4 of 4  
    Drug NameSitagliptin phosphate
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    Routeoral; Oral
    Strengtheq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
    Market StatusTentative Approval
    CompanyMylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Hypoglycemic Agents

    Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

    Incretins

    Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially. (See all compounds classified as Incretins.)

    Dipeptidyl-Peptidase IV Inhibitors

    Compounds that suppress the degradation of INCRETINS by blocking the action of DIPEPTIDYL-PEPTIDASE IV. This helps to correct the defective INSULIN and GLUCAGON secretion characteristic of TYPE 2 DIABETES MELLITUS by stimulating insulin secretion and suppressing glucagon release. (See all compounds classified as Dipeptidyl-Peptidase IV Inhibitors.)

    API Reference Price

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AP","supplier":"VERBEN S A","supplierCountry":"INDIA","foreign_port":"MUNICH","customer":"SMS PHARMACEUTICALS","customerCountry":"INDIA","quantity":"100.73","actualQuantity":"100.73","unit":"KGS","unitRateFc":"700","totalValueFC":"72156.1","currency":"USD","unitRateINR":"59709.3","date":"16-May-2024","totalValueINR":"6014513.38","totalValueInUsd":"72156.1","indian_port":"Hyderabad Air","hs_no":"29420090","bill_no":"3507838","productDescription":"Re-export","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"MUNICH","supplierAddress":"LUGANO BRANCHVIA F.PELLI 17P O BOX 6900 LUGANO CH","customerAddress":"PLOT NO.19-III, ROAD NO.71, OPP."},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1721154600,"product":"RE-IMPORT- SITAGLIPTIN PHOSPHATE (EXPORT INV NO:232410369 DT:30.03.2024 VIDE SB NO:8780352 DT: 30.03.2024 )","address":"26, VANDALUR - KELAMBAKKAM ROAD,","city":"CHENNAI. TAMIL NADU.","supplier":"DLS PHARMAG DMCC","supplierCountry":"INDIA","foreign_port":"DUBAI","customer":"VENKATA NARAYANA ACTIVE INGREDIENTS","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"325","totalValueFC":"332033.3","currency":"USD","unitRateINR":"27755","date":"17-Jul-2024","totalValueINR":"27755020.31","totalValueInUsd":"332033.3","indian_port":"Madras Air","hs_no":"29420090","bill_no":"4545754","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"DUBAI","supplierAddress":"2208,1 LAKE PLAZAJUMEIRAH LAKES TOWERSP B 309045 DUBAI UNITED ARAB EMIRATES","customerAddress":"26, VANDALUR - KELAMBAKKAM ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722450600,"product":"SITAGLIPTIN SYSTEM SUITABILITY MIXTURE (QTY: 3 X 0.05 G, VALUE USD: 17.60\/EACH) (FOC)","address":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"UNITED STATES PHARMACOPEIAL","supplierCountry":"INDIA","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.00015","unit":"KGS","unitRateFc":"352000","totalValueFC":"54.5","currency":"USD","unitRateINR":"30481066.7","date":"01-Aug-2024","totalValueINR":"4572.16","totalValueInUsd":"54.5","indian_port":"Hyderabad Air","hs_no":"29335990","bill_no":"4826736","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD, US 21704, UNITED STATES OF AMERICA United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1728412200,"product":"SITAGLIPTIN PHOSPHATE IP","address":"1544, LEVEL 15, EROS CORPORATE","city":"NEW DELHI","supplier":"DIVIS LABORATORIES LIMITED-DSN SEZ UNIT","supplierCountry":"INDIA","foreign_port":"DLL SEZ","customer":"MSD PHARMACEUTICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"1720.38","actualQuantity":"1720.38","unit":"KGS","unitRateFc":"404.2","totalValueFC":"702214.9","currency":"USD","unitRateINR":"34297.5","date":"09-Oct-2024","totalValueINR":"59004698.64","totalValueInUsd":"702214.9","indian_port":"Vizag-DLL SEZ","hs_no":"29335990","bill_no":"6032567","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"DLL SEZ","supplierAddress":"CHIPPADA VILLAGE ANNAVARAM POST BHEEMUNIPATNAM MANDAL VISAKHAPATNAM SDNF India","customerAddress":"1544, LEVEL 15, EROS CORPORATE"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729881000,"product":"SITAGLIPTIN PHOSPHATE ANH(SNP)CO USP(BR)","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"MYLAN LABORATORIES LIMITED FDF UNIT-3","supplierCountry":"INDIA","foreign_port":"NASIK","customer":"VIATRIS","customerCountry":"INDIA","quantity":"446.15","actualQuantity":"446.152","unit":"KGS","unitRateFc":"638.1","totalValueFC":"287835.8","currency":"USD","unitRateINR":"54209.9","date":"26-Oct-2024","totalValueINR":"24185846.38","totalValueInUsd":"287835.8","indian_port":"Indore-EPZ\/SEZ","hs_no":"29339990","bill_no":"6350764","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NASIK","supplierAddress":"IPlot No 11,12 & 13, SEZ Phase II SEZ, Sector 3, Pithampur, Dist Dhar SDNF India","customerAddress":"564\/A\/22, ROAD NO.92"}]
    04-Jan-2021
    30-Oct-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

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

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    INTERMEDIATES SUPPLIERS

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    01

    IOL Chemicals and Pharmaceuticals

    India
    CPhI India 2024
    Booth #1.C01
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    Virtual BoothIOL Chemicals is an innovation-driven bulk drug, Intermediate and Specialty Chemicals company.

    3- (Trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4] Tr...

    CAS Number : 762240-92-6

    End Use API : Sitagliptin Phosphate

    About The Company : With a history spanning over three decades, IOL Chemicals and Pharmaceuticals Limited is an innovation-driven company that specializes in bulk drugs, intermedia...

    IOL Chemicals

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    02

    Aptra Synthesis

    India
    CPhI India 2024
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    Virtual BoothAptra Synthesis produces APIs, Pellets (Semi-finished Formulations), and Intermediates.

    (2,4,5-trifIuorophenyI)acetic acid

    CAS Number : 209995-38-0

    End Use API : Sitagliptin Phosphate

    About The Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilit...

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    03

    Aptra Synthesis

    India
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    Virtual BoothAptra Synthesis produces APIs, Pellets (Semi-finished Formulations), and Intermediates.

    (3R)-3-Amino-1-[3-(trifIuoromethyI)-5,6,7,8-tetrah...

    CAS Number : 486460-32-6

    End Use API : Sitagliptin Phosphate

    About The Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilit...

    Aptra Synthesis

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    04

    Aptra Synthesis

    India
    CPhI India 2024
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    Virtual BoothAptra Synthesis produces APIs, Pellets (Semi-finished Formulations), and Intermediates.

    2,4,5-TrifIuoro-§-oxo-benzenebutanoic Acid Methyl...

    CAS Number : 769195-26-8

    End Use API : Sitagliptin Phosphate

    About The Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilit...

    Aptra Synthesis

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    05

    Aptra Synthesis

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    Virtual BoothAptra Synthesis produces APIs, Pellets (Semi-finished Formulations), and Intermediates.

    3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]tria...

    CAS Number : 762240-92-6

    End Use API : Sitagliptin Phosphate

    About The Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilit...

    Aptra Synthesis

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    06

    Aptra Synthesis

    India
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    Virtual BoothAptra Synthesis produces APIs, Pellets (Semi-finished Formulations), and Intermediates.

    Sitagliptin keto amide

    CAS Number : 764667-65-4

    End Use API : Sitagliptin Phosphate

    About The Company : Aptra Synthesis Private Limited, is a reliable and vertically integrated manufacturer of APIs and intermediates, boasting state-of-the-art manufacturing facilit...

    Aptra Synthesis

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    07

    Actis Generics Pvt Ltd

    India
    American Pharma Summit
    Not Confirmed
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    Actis Generics Pvt Ltd

    India
    American Pharma Summit
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    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.

    3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]tria...

    CAS Number : 762240-92-6

    End Use API : Sitagliptin Phosphate

    About The Company : Actis Generics Pvt Ltd is a fast emerging APIs (Active Pharmaceutical Ingredients) & Intermediates manufacturer & supplier in India set up by a group of young p...

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    08

    Actis Generics Pvt Ltd

    India
    American Pharma Summit
    Not Confirmed
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    Actis Generics Pvt Ltd

    India
    American Pharma Summit
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    (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2...

    CAS Number : 764667-65-4

    End Use API : Sitagliptin Phosphate

    About The Company : Actis Generics Pvt Ltd is a fast emerging APIs (Active Pharmaceutical Ingredients) & Intermediates manufacturer & supplier in India set up by a group of young p...

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    Portfolio PDF

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    09

    Actis Generics Pvt Ltd

    India
    American Pharma Summit
    Not Confirmed
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    Actis Generics Pvt Ltd

    India
    American Pharma Summit
    Not Confirmed
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    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.

    (3R)-3-Amino-1-[3-(trifluoromethyl)-5,6,7,8-tetrah...

    CAS Number : 486460-32-6

    End Use API : Sitagliptin Phosphate

    About The Company : Actis Generics Pvt Ltd is a fast emerging APIs (Active Pharmaceutical Ingredients) & Intermediates manufacturer & supplier in India set up by a group of young p...

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    10

    Almelo

    India
    American Pharma Summit
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    Almelo

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    3-(Trifluoromethyl)-5,6,7,8- Tetrahydro-[1,2,4] Tr...

    CAS Number : CAS-762240-92-6

    End Use API : Sitagliptin Phosphate

    About The Company : Almelo are the industry leaders in manufacturing advanced intermediates, Active Pharmaceutical Ingredients (APIs) and specialty fine chemicals. With a diverse p...

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - EQ 100MG BASE

    USFDA APPLICATION NUMBER - 21995

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    DOSAGE - TABLET;ORAL - EQ 25MG BASE

    USFDA APPLICATION NUMBER - 21995

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    DOSAGE - TABLET;ORAL - EQ 50MG BASE

    USFDA APPLICATION NUMBER - 21995

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    DOSAGE - TABLET;ORAL - 1GM;EQ 50MG BASE

    USFDA APPLICATION NUMBER - 22044

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    DOSAGE - TABLET;ORAL - 500MG;EQ 50MG BASE

    USFDA APPLICATION NUMBER - 22044

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