User:Mr. Ibrahem/Ergotamine

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Mr. Ibrahem/Ergotamine
Clinical data
Trade namesAlone: Ergomar, others
With caffeine: Cafergot, others
Other names2'-Methyl-5'α-benzyl-12'-hydroxy-3',6',18-trioxoergotaman; 9,10α-Dihydro-12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
AHFS/Drugs.comMonograph
Routes of
administration		By mouth, under the tongue[1]
Legal status
Legal status
Pharmacokinetic data
BioavailabilityIntravenous: 100%,[2]
Intramuscular: 47%,[3]
By mouth: <1%[4] (Enhanced by co-administration of caffeine[2])
MetabolismLiver[3]
Elimination half-life2 hours[3]
Excretion90% biliary[3]
Identifiers
  • (6aR,9R)-N-((2R,5S,10aS,10bS)-5-Benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
FormulaC33H35N5O5
Molar mass581.673 g·mol−1
3D model (JSmol)
  • C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C
  • InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1 checkY
  • Key:XCGSFFUVFURLIX-VFGNJEKYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ergotamine, sold under the brand names Ergomar among others, is a medication used to treat migraines, cluster headaches, and post partum bleeding.[1][6] It is not effective for tension headaches.[1] It is taken by mouth, under the tongue, or rectally.[1][7] Onset of effects is generally between 30 minutes and 2 hours.[8]

Common side effects include nausea, abdominal pain, and tingling extremities.[1] Other side effects may include medication overuse headaches, pulmonary fibrosis, and ergotism.[9][1] Use in pregnancy or when breastfeeding may harm the baby.[5] It is not recommended in people with vascular disease, liver, or kidney problems.[9] It is in the ergot family of medications and acts on serotonin among other receptors.[9][8]

Ergotamine was first isolated by Arthur Stoll in 1918 from ergot fungus.[10] The fungus had been used medicinally since at least the 16th century to induce childbirth, treat bleeding after childbirth, or bring about an abortion.[11] In the United States it is generally only used if triptans are not effective; though remains commonly used in some parts of the world.[9] It is also available with caffeine under the brand Cafergot among others.[1]

References[edit]

  1. ^ a b c d e f g h i j "Ergotamine Monograph for Professionals". Drugs.com. Archived from the original on 27 January 2021. Retrieved 23 July 2021.
  2. ^ a b Sanders SW, Haering N, Mosberg H, Jaeger H (1986). "Pharmacokinetics of ergotamine in healthy volunteers following oral and rectal dosing". European Journal of Clinical Pharmacology. 30 (3): 331–4. doi:10.1007/BF00541538. PMID 3732370. S2CID 37538721.
  3. ^ a b c d Tfelt-Hansen P, Johnson ES (1993). "Ergotamine". In Olesen J, Tfelt-Hansen P, Welch KM (eds.). The Headaches. New York: Raven Press. pp. 313–22.
  4. ^ Ibraheem JJ, Paalzow L, Tfelt-Hansen P (December 1983). "Low bioavailability of ergotamine tartrate after oral and rectal administration in migraine sufferers". British Journal of Clinical Pharmacology. 16 (6): 695–9. doi:10.1111/j.1365-2125.1983.tb02243.x. PMC 1428366. PMID 6419759.
  5. ^ a b "Ergotamine (Ergomar) Use During Pregnancy". Drugs.com. Archived from the original on 25 November 2020. Retrieved 23 July 2021.
  6. ^ Weeks, A (January 2015). "The prevention and treatment of postpartum haemorrhage: what do we know, and where do we go to next?". BJOG : An International Journal of Obstetrics and Gynaecology. 122 (2): 202–10. doi:10.1111/1471-0528.13098. PMID 25289730.
  7. ^ BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 500. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
  8. ^ a b Aschenbrenner, Diane S.; Venable, Samantha J. (2009). Drug Therapy in Nursing. Lippincott Williams & Wilkins. p. 423. ISBN 978-0-7817-6587-9. Archived from the original on 2021-08-28. Retrieved 2021-07-23.
  9. ^ a b c d Levin, Morris (8 May 2008). Comprehensive Review of Headache Medicine. Oxford University Press, USA. p. 217. ISBN 978-0-19-536673-0. Archived from the original on 28 August 2021. Retrieved 23 July 2021.
  10. ^ Silberstein, Stephen D. (8 May 2018). Headache in Clinical Practice. Routledge. p. PT19. ISBN 978-1-351-44131-5. Archived from the original on 28 August 2021. Retrieved 23 July 2021.
  11. ^ Nielsch, Ulrich; Fuhrmann, Ulrike; Jaroch, Stefan (30 March 2016). New Approaches to Drug Discovery. Springer. p. PA6. ISBN 978-3-319-28914-4. Archived from the original on 28 August 2021. Retrieved 23 July 2021.
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