Gosogliptin

Gosogliptin
INN: Gosogliptin
Clinical data
Other names	PF-734200
Identifiers
	IUPAC name (3,3-Difluoro-1-pyrrolidinyl){(2S,4S)-4-[4-(2-pyrimidinyl)-1-piperazinyl]-2-pyrrolidinyl}methanone;
CAS Number	869490-23-3;
PubChem CID	11516136;
DrugBank	DB08382;
ChemSpider	9690926;
UNII	GI718UO477;
CompTox Dashboard (EPA)	DTXSID601007213 ;
Chemical and physical data
Formula	C17H24F2N6O
Molar mass	366.417 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cnc(nc1)N2CCN(CC2)[C@H]3C[C@H](NC3)C(=O)N4CCC(C4)(F)F;
	InChI InChI=1S/C17H24F2N6O/c18-17(19)2-5-25(12-17)15(26)14-10-13(11-22-14)23-6-8-24(9-7-23)16-20-3-1-4-21-16/h1,3-4,13-14,22H,2,5-12H2/t13-,14-/m0/s1; Key:QWEWGXUTRTXFRF-KBPBESRZSA-N;

Gosogliptin (INN; trade name SatRx) is a drug for the treatment of type II diabetes. It is in the class of dipeptidyl peptidase-4 (DPP-4) inhibitors (also called gliptins). It was discovered[1] and developed through Phase 1[2][3][4] and Phase 2[5][6][7]by Pfizer. The crystal structure of DPP-4 in complex with gosogliptin is available.[8] Its metabolism, excretion and pharmacokinetics in rat, dog and human have been described.[9] A cost efficient route has been published.[10] Other studies[11] including Phase 3 studies were conducted in Russia.[12][13] It is approved for use in Russia.[14]

References

Ammirati MJ, Andrews KM, Boyer DD, Brodeur AM, Danley DE, Doran SD, Hulin B, Liu S, McPherson RK, Orena SJ, Parker JC, Polivkova J, Qiu X, Soglia CB, Treadway JL, VanVolkenburg MA, Wilder DC, Piotrowski DW (April 2009). "(3,3-Difluoro-pyrrolidin-1-yl)-[(2S,4S)-(4-(4-pyrimidin-2-yl-piperazin-1-yl)-pyrrolidin-2-yl]-methanone: a potent, selective, orally active dipeptidyl peptidase IV inhibitor". Bioorganic & Medicinal Chemistry Letters. 19 (7): 1991–1995. doi:10.1016/j.bmcl.2009.02.041. PMID 19275964.
Dai H, Gustavson SM, Preston GM, Eskra JD, Calle R, Hirshberg B (2008). "Non-linear increase in GLP-1 levels in response to DPP-IV inhibition in healthy adult subjects". Diabetes, Obesity, and Metabolism. 10: 506–513. doi:10.1111/j.1463-1326.2007.00742.x.
Dai H, Johnson SL, Terra SG, Marbury TC, Smith WB, Alcorn H, Boyd RA, Wang R, Nguyen TT (July 2011). "The pharmacokinetics of PF-734200, a DPP-IV inhibitor, in subjects with renal insufficiency". British Journal of Clinical Pharmacology. 72 (1): 85–91. doi:10.1111/j.1365-2125.2011.03954.x. PMC 3141189. PMID 21366665.
Muto C, Dai H, Teeter JG, Johnson S, Cropp AB, Chiba K, Suwa T (2012). "The pharmacokinetics and pharmacodynamics of PF-00734200, a DPP-IV inhibitor, in healthy Japanese subjects". International Journal of Clinical Pharmacology and Therapeutics. 50: 505–509. doi:10.5414/CP201614.
Rosenstock J, Lewin AJ, Norwood P, Somayaji V, Nguyen TT, Teeter JG, Johnson SL, Dai H, Terra SG (2011). "Efficacy and safety of the dipeptidyl peptidase‐4 inhibitor PF‐734200 added to metformin in Type 2 diabetes". Diabetic Medicine. 28: 464–469. doi:10.1111/j.1464-5491.2010.03181.x.
https://clinicaltrials.gov/ct2/show/NCT00618007
https://clinicaltrials.gov/ct2/show/NCT00473525
https://www.rcsb.org/structure/3F8S
Sharma R, Sun H, Piotrowski DW, Ryder TF, Doran SD, Dai H, Prakash C (November 2012). "Metabolism, Excretion, and Pharmacokinetics of ((3,3-Difluoropyrrolidin-1-yl)((2 S ,4 S )-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a Dipeptidyl Peptidase Inhibitor, in Rat, Dog and Human". Drug Metabolism and Disposition. 40 (11): 2143–2161. doi:10.1124/dmd.112.047316. ISSN 0090-9556.
Lafrance D, Caron S (January 2012). "New Synthetic Route to a Dipeptidyl Peptidase-4 Inhibitor". Organic Process & Research Development. 16 (3): 409–14. doi:10.1021/op200309z.
Nedosugova LV, Petunina NA, Galstyan KO (2014). "Initial investigation of efficacy and safety of a new dipeptidyl peptidase-4 inhibitor, gosogliptin, for type 2 diabetes in Russia". Diabetes mellitus. 17 (4). doi:10.14341/DM2014481-86.
Galstyan KO, Nedosugova LV, Petunina NA, Trakhtenberg JA, Vostokova NV, Karavaeva OV, Chasovskaya TE (April 2016). "Comparison of the novel Russian DPP-4 inhibitor gosogliptin with vildagliptin in patients with type 2 diabetes mellitus". Diabetes mellitus. 19 (1): 89‐96. doi:10.14341/DM7233.
https://clinicaltrials.gov/ct2/show/NCT03088670
"SatRx LLC Announces First Registration in Russia of SatRx (gosogliptin), an Innovative Drug for Treatment of Type 2 Diabetes" (Press release). SatRx LLC.

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[1] Ammirati MJ, Andrews KM, Boyer DD, Brodeur AM, Danley DE, Doran SD, Hulin B, Liu S, McPherson RK, Orena SJ, Parker JC, Polivkova J, Qiu X, Soglia CB, Treadway JL, VanVolkenburg MA, Wilder DC, Piotrowski DW (April 2009). "(3,3-Difluoro-pyrrolidin-1-yl)-[(2S,4S)-(4-(4-pyrimidin-2-yl-piperazin-1-yl)-pyrrolidin-2-yl]-methanone: a potent, selective, orally active dipeptidyl peptidase IV inhibitor". Bioorganic & Medicinal Chemistry Letters. 19 (7): 1991–1995. doi:10.1016/j.bmcl.2009.02.041. PMID 19275964.

[2] Dai H, Gustavson SM, Preston GM, Eskra JD, Calle R, Hirshberg B (2008). "Non-linear increase in GLP-1 levels in response to DPP-IV inhibition in healthy adult subjects". Diabetes, Obesity, and Metabolism. 10: 506–513. doi:10.1111/j.1463-1326.2007.00742.x.

[3] Dai H, Johnson SL, Terra SG, Marbury TC, Smith WB, Alcorn H, Boyd RA, Wang R, Nguyen TT (July 2011). "The pharmacokinetics of PF-734200, a DPP-IV inhibitor, in subjects with renal insufficiency". British Journal of Clinical Pharmacology. 72 (1): 85–91. doi:10.1111/j.1365-2125.2011.03954.x. PMC 3141189. PMID 21366665.

[4] Muto C, Dai H, Teeter JG, Johnson S, Cropp AB, Chiba K, Suwa T (2012). "The pharmacokinetics and pharmacodynamics of PF-00734200, a DPP-IV inhibitor, in healthy Japanese subjects". International Journal of Clinical Pharmacology and Therapeutics. 50: 505–509. doi:10.5414/CP201614.

[5] Rosenstock J, Lewin AJ, Norwood P, Somayaji V, Nguyen TT, Teeter JG, Johnson SL, Dai H, Terra SG (2011). "Efficacy and safety of the dipeptidyl peptidase‐4 inhibitor PF‐734200 added to metformin in Type 2 diabetes". Diabetic Medicine. 28: 464–469. doi:10.1111/j.1464-5491.2010.03181.x.

[6] ttps://clinicaltrials.gov/ct2/show/NCT00618007

[7] ttps://clinicaltrials.gov/ct2/show/NCT00473525

[8] ttps://www.rcsb.org/structure/3F8S

[9] Sharma R, Sun H, Piotrowski DW, Ryder TF, Doran SD, Dai H, Prakash C (November 2012). "Metabolism, Excretion, and Pharmacokinetics of ((3,3-Difluoropyrrolidin-1-yl)((2 S ,4 S )-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidin-2-yl)methanone, a Dipeptidyl Peptidase Inhibitor, in Rat, Dog and Human". Drug Metabolism and Disposition. 40 (11): 2143–2161. doi:10.1124/dmd.112.047316. ISSN 0090-9556.

[10] Lafrance D, Caron S (January 2012). "New Synthetic Route to a Dipeptidyl Peptidase-4 Inhibitor". Organic Process & Research Development. 16 (3): 409–14. doi:10.1021/op200309z.

[11] Nedosugova LV, Petunina NA, Galstyan KO (2014). "Initial investigation of efficacy and safety of a new dipeptidyl peptidase-4 inhibitor, gosogliptin, for type 2 diabetes in Russia". Diabetes mellitus. 17 (4). doi:10.14341/DM2014481-86.

[12] Galstyan KO, Nedosugova LV, Petunina NA, Trakhtenberg JA, Vostokova NV, Karavaeva OV, Chasovskaya TE (April 2016). "Comparison of the novel Russian DPP-4 inhibitor gosogliptin with vildagliptin in patients with type 2 diabetes mellitus". Diabetes mellitus. 19 (1): 89‐96. doi:10.14341/DM7233.

[13] ttps://clinicaltrials.gov/ct2/show/NCT03088670

[14] "SatRx LLC Announces First Registration in Russia of SatRx (gosogliptin), an Innovative Drug for Treatment of Type 2 Diabetes" (Press release). SatRx LLC.