Hyoscine butylbromide

Hyoscine butylbromide
Clinical data
Trade names	Buscopan
Pregnancy; category	AU: B2; ;
Routes of; administration	Oral, rectal, intravenous
ATC code	A03BB01 (WHO) ;
Legal status
Legal status	AU: S2 (Pharmacy medicine); UK: General sales list (GSL, OTC);
Pharmacokinetic data
Bioavailability	<1%
Protein binding	Low
Elimination half-life	5 hours
Excretion	Renal (50%) [citation needed] and fecal
Identifiers
	IUPAC name [7(S)-(1α,2β,4β,5α,7β)]-9-butyl-7-(3-hydroxy-; 1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-; 9-azonitricyclo[3.3.1.0(2,4)]nonane;
CAS Number	149-64-4 ;
PubChem CID	160883;
DrugBank	DB09300 ;
ChemSpider	16736107 ;
UNII	2Z3E1OF81V;
ChEMBL	ChEMBL1256901 ;
CompTox Dashboard (EPA)	DTXSID1022718 ;
ECHA InfoCard	100.005.223
Chemical and physical data
Formula	C21H30NO4+
Molar mass	360.467 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [Br-].OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@@H]3[C@H]4O[C@H]4[C@H](C2)[N+]3(C)CCCC;
	InChI InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1 ; Key:HOZOZZFCZRXYEK-GSWUYBTGSA-M ;
	(what is this?) (verify)

Hyoscine butylbromide, also known as scopolamine butylbromide^[1] and sold under the brandname Buscopan,^[2] is a medication used to treat crampy abdominal pain, renal colic, and bladder spasms.^[2]^[3] It is also used to improve a death rattle at the end of life.^[4] Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.^[2]

Side effects may include sleepiness, vision changes, triggering of glaucoma, and severe allergies.^[2] Sleepiness however, is uncommon.^[5] It is unclear if it is safe in pregnancy.^[2] It is an anticholinergic agent,^[2] which does not have much effect on the brain.^[6]

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.^[7] It is not available in the United States.^[8] The wholesale cost is 0.004 to 0.11 USD per pill as of 2014.^[9] It is manufactured from hyoscine which is naturally from the plant deadly nightshade.^[10]

Medical uses

Hyoscine butylbromide is used to treat crampy abdominal pain with some success.^[11]

Hyoscine butylbromide is effective in significantly reducing the duration of the first stage of labour, and it is not associated with any obvious adverse outcomes in mother or neonate.^[12]

Pharmacology

It is a quaternary ammonium compound and a semisynthetic derivative of scopolamine. The attachment of the butyl-bromide moiety effectively prevents the movement of this drug across the blood–brain barrier, effectively minimising undesirable central nervous system side effects associated with scopolamine/hyoscine.

Abuse

Hyoscine butylbromide is not centrally active and has a low incidence of abuse.

Names

Other names include butylscopolamine, scopolamine butylbromide,^[1] butylhyoscine, and butylscopolamine bromide.

References

^ ^a ^b Juo, Pei-Show (2001). Concise Dictionary of Biomedicine and Molecular Biology (2nd ed.). Hoboken: CRC Press. p. 570. ISBN 9781420041309.
^ ^a ^b ^c ^d ^e ^f "BUSCOPAN Tablets and Ampoules BUSCOPAN FORTE Tablets". TGA eBusiness Services. BOEHRINGER INGELHEIM PTY LIMITED. 8 November 2010. Retrieved 22 October 2013.
^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560.
^ Paice, Judith (2015). Care of the Imminently Dying. Oxford University Press. p. 43. ISBN 9780190244309.
^ Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814.
^ Hanks, Geoffrey (2011). Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. p. 805. ISBN 9780199693146.
^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
^ Territo, editor, Dennis A. Casciato ; associate editor, Mary C. (2012). Manual of clinical oncology (7th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health. p. 146. ISBN 9781451115604. {{cite book}}: |first1= has generic name (help)CS1 maint: multiple names: authors list (link)
^ "Hyoscine Butylbromide". International Drug Price Indicator Guide. Retrieved 4 December 2015.
^ Twycross, Robert (2003). Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. p. 172. ISBN 9781857759150.
^ Tytgat, G. N. (2007). "Hyoscine Butylbromide: A Review of its Use in the Treatment of Abdominal Cramping and Pain". Drugs. 67 (9): 1343–1357. doi:10.2165/00003495-200767090-00007. PMID 17547475.
^ Samuels, L. A.; Christie, L.; Roberts-Gittens, B.; Fletcher, H.; Frederick, J. (2007). "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies". BJOG. 114 (12): 1542–1546. doi:10.1111/j.1471-0528.2007.01497.x. PMID 17903230.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

"Buscopan / Buscapina". Boehringer Ingelheim.

[Huo2001-1] Juo, Pei-Show (2001). Concise Dictionary of Biomedicine and Molecular Biology (2nd ed.). Hoboken: CRC Press. p. 570. ISBN 9781420041309.

[TGA2010-2] ^ ^a ^b ^c ^d ^e ^f "BUSCOPAN Tablets and Ampoules BUSCOPAN FORTE Tablets". TGA eBusiness Services. BOEHRINGER INGELHEIM PTY LIMITED. 8 November 2010. Retrieved 22 October 2013.

[Ric2015-3] Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 270. ISBN 9781284057560.

[4] Paice, Judith (2015). Care of the Imminently Dying. Oxford University Press. p. 43. ISBN 9780190244309.

[5] Handbook of Palliative Care (3rd ed.). New York: Wiley. 2012. p. 570. ISBN 9781118426814.

[6] Hanks, Geoffrey (2011). Oxford textbook of palliative medicine (4th ed.). Oxford [etc.]: Oxford University Press. p. 805. ISBN 9780199693146.

[7] "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[8] Territo, editor, Dennis A. Casciato ; associate editor, Mary C. (2012). Manual of clinical oncology (7th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health. p. 146. ISBN 9781451115604. {{cite book}}: |first1= has generic name (help)CS1 maint: multiple names: authors list (link)

[9] "Hyoscine Butylbromide". International Drug Price Indicator Guide. Retrieved 4 December 2015.

[10] Twycross, Robert (2003). Introducing palliative care (4th ed.). Oxford: Radcliffe Medical Press. p. 172. ISBN 9781857759150.

[11] Tytgat, G. N. (2007). "Hyoscine Butylbromide: A Review of its Use in the Treatment of Abdominal Cramping and Pain". Drugs. 67 (9): 1343–1357. doi:10.2165/00003495-200767090-00007. PMID 17547475.

[12] Samuels, L. A.; Christie, L.; Roberts-Gittens, B.; Fletcher, H.; Frederick, J. (2007). "The effect of hyoscine butylbromide on the first stage of labour in term pregnancies". BJOG. 114 (12): 1542–1546. doi:10.1111/j.1471-0528.2007.01497.x. PMID 17903230.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]