Atosiban

Atosiban
Clinical data
Trade names	Tractocile, Antocin, others
AHFS/Drugs.com	UK Drug Information
License data	EU EMA: by INN;
Routes of; administration	Intravenous
ATC code	G02CX01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); EU: Rx-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-(3-Mercaptopropanoic acid)-; 2-(O-ethyl-D-tyrosine)-4-L-threonine-; 8-L-ornithine-oxytocin;
CAS Number	90779-69-4 ;
PubChem CID	5311010;
IUPHAR/BPS	2213;
DrugBank	DB09059;
ChemSpider	4470550 ;
UNII	081D12SI0Z;
KEGG	D03008 ;
ChEMBL	ChEMBL378642 ;
CompTox Dashboard (EPA)	DTXSID8048991 ;
ECHA InfoCard	100.234.128
Chemical and physical data
Formula	C43H67N11O12S2
Molar mass	994.19 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]3N(C(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CCSSC1)Cc2ccc(OCC)cc2)[C@@H](C)CC)[C@H](O)C)CC(=O)N)CCC3)CCCN;
	InChI InChI=1S/C43H67N11O12S2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1 ; Key:VWXRQYYUEIYXCZ-OBIMUBPZSA-N ;
	(what is this?) (verify)

Atosiban, sold under the brand name Tractocile among others, is an inhibitor of the hormones oxytocin and vasopressin. It is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor. It was developed by Ferring Pharmaceuticals in Sweden and first reported in the literature in 1985.^[5] Originally marketed by Ferring Pharmaceuticals, it is licensed in proprietary and generic forms for the delay of imminent preterm birth in pregnant adult women.

The most commonly reported side effect is nausea.^[4]

^ "Atosiban International Drug Names". Drugs.com. 10 April 2020. Archived from the original on 27 December 2019. Retrieved 29 April 2020.
^ "Tractocile 7.5 mg/ml Solution for Injection - Summary of Product Characteristics (SmPC)". (emc). Retrieved 29 April 2020.
^ "Tractocile 7.5 mg/ml Concentrate for Solution for Infusion - Summary of Product Characteristics (SmPC)". (emc). 24 June 2013. Retrieved 29 April 2020.
^ ^a ^b Cite error: The named reference Tractocile EPAR was invoked but never defined (see the help page).
^ Akerlund M, Carlsson AM, Melin P, Trojnar J (1985). "The effect on the human uterus of two newly developed competitive inhibitors of oxytocin and vasopressin". Acta Obstetricia et Gynecologica Scandinavica. 64 (6): 499–504. doi:10.3109/00016348509156728. PMID 4061066. S2CID 25799128.

[1] "Atosiban International Drug Names". Drugs.com. 10 April 2020. Archived from the original on 27 December 2019. Retrieved 29 April 2020.

[2] "Tractocile 7.5 mg/ml Solution for Injection - Summary of Product Characteristics (SmPC)". (emc). Retrieved 29 April 2020.

[3] "Tractocile 7.5 mg/ml Concentrate for Solution for Infusion - Summary of Product Characteristics (SmPC)". (emc). 24 June 2013. Retrieved 29 April 2020.

[Tractocile_EPAR-4] Cite error: The named reference Tractocile EPAR was invoked but never defined (see the help page).

[5] Akerlund M, Carlsson AM, Melin P, Trojnar J (1985). "The effect on the human uterus of two newly developed competitive inhibitors of oxytocin and vasopressin". Acta Obstetricia et Gynecologica Scandinavica. 64 (6): 499–504. doi:10.3109/00016348509156728. PMID 4061066. S2CID 25799128.

[1]

[2]

[3]

[4]

[5]

Clinical data

Trade names	Tractocile, Antocin, others^[1]
AHFS/Drugs.com	UK Drug Information
License data	EU EMA: by INN
Routes of administration	Intravenous
ATC code	G02CX01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)^[2]^[3] EU: Rx-only^[4] In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-(3-Mercaptopropanoic acid)- 2-(O-ethyl-D-tyrosine)-4-L-threonine- 8-L-ornithine-oxytocin
CAS Number	90779-69-4^N
PubChem CID	5311010
IUPHAR/BPS	2213
DrugBank	DB09059
ChemSpider	4470550^Y
UNII	081D12SI0Z
KEGG	D03008^Y
ChEMBL	ChEMBL378642^N
CompTox Dashboard (EPA)	DTXSID8048991
ECHA InfoCard	100.234.128
Chemical and physical data
Formula	C₄₃H₆₇N₁₁O₁₂S₂
Molar mass	994.19 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]3N(C(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CCSSC1)Cc2ccc(OCC)cc2)[C@@H](C)CC)[C@H](O)C)CC(=O)N)CCC3)CCCN
InChI InChI=1S/C43H67N11O12S2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1^Y Key:VWXRQYYUEIYXCZ-OBIMUBPZSA-N^Y
^NY (what is this?) (verify)