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Tetracosactide

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Tetracosactide
Clinical data
Other namesBa 30920
α1–24 corticotrophin
Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-Lys-Lys-Arg-Arg-Pro-Val-Lys-Val-Tyr-Pro
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • L-seryl-L-tyrosyl-L-seryl-L-methionyl-L-α-glutamyl-L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycyl-L-lysyl-L-prolyl-L-valylglycyl-L-lysyl-L-lysyl-L-arginyl-L-arginyl-L-prolyl-L-valyl-L-lysyl-L-valyl-L-tyrosyl-L-proline
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
Chemical and physical data
FormulaC136H210N40O31S
Molar mass2933.44 g/mol g·mol−1
  • InChI=1S/C136H210N40O31S/c1-75(2)109(127(200)154-71-106(181)156-88(31-13-17-52-137)114(187)158-89(32-14-18-53-138)115(188)159-91(35-21-56-149-134(142)143)116(189)164-96(37-23-58-151-136(146)147)131(204)175-60-25-39-104(175)126(199)173-111(77(5)6)128(201)163-90(33-15-19-54-139)120(193)171-110(76(3)4)129(202)169-101(65-80-43-47-84(180)48-44-80)132(205)176-61-26-40-105(176)133(206)207)172-125(198)103-38-24-59-174(103)130(203)95(34-16-20-55-140)157-107(182)70-153-113(186)99(66-81-68-152-87-30-12-11-29-85(81)87)167-117(190)92(36-22-57-150-135(144)145)160-121(194)98(63-78-27-9-8-10-28-78)166-123(196)100(67-82-69-148-74-155-82)168-118(191)93(49-50-108(183)184)161-119(192)94(51-62-208-7)162-124(197)102(73-178)170-122(195)97(165-112(185)86(141)72-177)64-79-41-45-83(179)46-42-79/h8-12,27-30,41-48,68-69,74-77,86,88-105,109-111,152,177-180H,13-26,31-40,49-67,70-73,137-141H2,1-7H3,(H,148,155)(H,153,186)(H,154,200)(H,156,181)(H,157,182)(H,158,187)(H,159,188)(H,160,194)(H,161,192)(H,162,197)(H,163,201)(H,164,189)(H,165,185)(H,166,196)(H,167,190)(H,168,191)(H,169,202)(H,170,195)(H,171,193)(H,172,198)(H,173,199)(H,183,184)(H,206,207)(H4,142,143,149)(H4,144,145,150)(H4,146,147,151)/t86?,88-,89-,90+,91-,92+,93+,94+,95+,96-,97+,98+,99+,100+,101+,102+,103+,104+,105+,109+,110+,111+/m1/s1 ☒N
  • Key:ZOEFCCMDUURGSE-CQVUSSRSSA-N ☒N
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Tetracosactide (INN) (brand names Synacthen, Cortrosyn), also known as tetracosactrin (BAN) and cosyntropin (USAN), and the acetate ester, tetracosactide acetate (JAN) (brand names Cortrosina, Cortrosyn, Nuvacthen, Synacthen), also known as tetracosactrin acetate (BANM), is a synthetic peptide and analogue of adrenocorticotrophic hormone (ACTH) which is used clinically as a diagnostic agent.[1][2][3] It consists of the first 24 (of a total of 39) amino acids of ACTH and retains full function of the parent peptide.[1][4] Tetracosactide stimulates the release of corticosteroids such as cortisol from the adrenal glands, and is used for the ACTH stimulation test to assess adrenal gland function.[2]

Uses

Tetracosactide is used for diagnostic purposes (e.g. in short synacthen test). It is suitable for treatment of adrenal insufficiency of central origin. Synacthen is also being used in treatment of different types of drug registant epilepsia, particularly by pediatric neurologists.

In patients with low cortisol levels or symptoms of adrenocortical insufficiency, tetracosactide can be used to diagnose Addison's disease. A failure for serum cortisol levels to increase after administration of tetracosactide makes a diagnosis of primary adrenocortical insufficiency more likely. An increase in cortisol upon administration of tetracosactide rules out the condition. The test may also be used to assess the function of the adrenal glands after successful treatment for Cushing's syndrome.

Tetracosactide is also used in the opposite situation, when there is aldosterone hypersecretion due to either a unilateral adrenal adenoma (which is treated by surgical removal) or bilateral adrenal hyperplasia (treated by oral spironolactone). A procedure called adrenal venous sampling may be used pre-operatively to localize the source of aldosterone hypersecretion from either adrenal gland. A peripheral intravenous infusion of tetracosactide before and during the procedure stimulates cortisol production and thereby verifies catheter position.[5]

As well as its legitimate medical applications, it has been widely reported that tetracosactide has also been used as an illegal performance-enhancing drug by professional cyclists.[6] It is known to be used as a doping agent to increase the secretion of glucocorticoids by adrenal glands.[7]

Tetracosactide has been used in the treatment of infantile spasms.[8]

Types of drug resistant epilepsy that can be treated with Synacthen:

Pharmacology

In the normal situation, ACTH is released from the pituitary gland at the base of the brain. It acts on the adrenal glands to stimulate the production of steroid hormones (glucocorticoids). If the adrenal glands are healthy, a single injection of tetracosactide results in a rise in blood cortisol (hydrocortisone) concentrations in 30 minutes. If the adrenal glands appear not to be working then tetracosactide injection can be given to check whether the problem is due to diseased or damaged adrenals or due to lack of pituitary ACTH.

Politics

Synacthen Depot's pricing increased by 2000% in 2015 in Canadian jurisdictions, causing some provincial single payer authorities to delist the drug from funded medications. The increase in the drug's price came after Mallinckrodt acquired Questcor and its drug portfolio, which included the worldwide rights to Synacthen Depot. Prior to the price increase, Mallinckrodt claims that the drug was manufactured at a loss. Some have claimed that the price increase is abusive.[9] The drug had been priced at $33 but rose to $680 per vial. As an off-patent pharmaceutical, a similar drug, differing in formulation, available in Europe, made by a different manufacturer, sells for $8 per vial.[10]

See also

References

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1165–. ISBN 978-1-4757-2085-3.
  2. ^ a b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 271–. ISBN 978-94-011-4439-1.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1005–. ISBN 978-3-88763-075-1.
  4. ^ Cortrosyn information
  5. ^ Carr, CE; Cope, C; Cohen, DL; Fraker, DL; Trerotola, SO (Nov 2004). "Comparison of sequential versus simultaneous methods of adrenal venous sampling". Journal of vascular and interventional radiology : JVIR. 15 (11): 1245–50. doi:10.1097/01.RVI.0000134495.26900.6A. PMID 15525743.
  6. ^ Kimmage P (2007). "tour 87 stage 14". Rough Ride. Yellow Jersey Press. p. 125. ISBN 0-224-08017-2.
  7. ^ Chaabo A, de Ceaurriz J, Buisson C, Tabet JC, Lasne F (February 2011). "Simultaneous quantification and qualification of synacthen in plasma". Anal Bioanal Chem. 399 (5): 1835–43. doi:10.1007/s00216-010-4565-z. PMID 21170520.
  8. ^ Lux AL, Edwards SW, Hancock E, Johnson AL, Kennedy CR, Newton RW, O'Callaghan FJ, Verity CM, Osborne JP (2004). "The United Kingdom Infantile Spasms Study comparing vigabatrin with prednisolone or tetracosactide at 14 days: a multicentre, randomised controlled trial". Lancet. 364 (9447): 1773–8. doi:10.1016/S0140-6736(04)17400-X. PMID 15541450.
  9. ^ Kelly Crowe (16 November 2015). "2,000% price hike for infant seizure drug called 'absurd'". CBC News.
  10. ^ "Monday November 16th 2015". The National. CBC News. 16 November 2015.