Paromomycin

Paromomycin
Clinical data
Trade names	Catenulin, Aminosidine, Humatin, others
Other names	monomycin, aminosidine
AHFS/Drugs.com	Monograph
MedlinePlus	a601098
License data	US DailyMed: Paromomycin;
Pregnancy; category	C;
Routes of; administration	By mouth, intramuscular, topical
ATC code	A07AA06 (WHO) ; QJ01GB92 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	Poorly absorbed in the GI tract
Metabolism	Not available
Excretion	Fecal
Identifiers
	IUPAC name (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2S,3S,4R,6S)-; 4,6-diamino-2-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-; 3-amino-6-(aminomethyl)-4,5-dihydroxy-oxan-2-yl]; oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-; 3-hydroxy-cyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol;
CAS Number	1263-89-4 ;
PubChem CID	441375;
DrugBank	DB01421 ;
ChemSpider	390117 ;
UNII	845NU6GJPS;
ChEBI	CHEBI:7934 ;
ChEMBL	ChEMBL370143 ;
CompTox Dashboard (EPA)	DTXSID8023424 ;
ECHA InfoCard	100.028.567
Chemical and physical data
Formula	C23H47N5O18S
Molar mass	713.71 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(O)O.O([C@H]3[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@H]1O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]1N)[C@H]2O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4N)CO;
	InChI InChI=1S/C23H45N5O14.H2O4S/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1 ; Key:LJRDOKAZOAKLDU-UDXJMMFXSA-N ;
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Paromomycin is an antimicrobial used to treat a number of parasitic infections including amebiasis, giardiasis, leishmaniasis, and tapeworm infection.^[3] It is a first-line treatment for amebiasis or giardiasis during pregnancy.^[3] Otherwise, it is generally a second line treatment option.^[3] It is taken by mouth, applied to the skin, or by injection into a muscle.^[3]

Common side effects when taken by mouth include loss of appetite, vomiting, abdominal pain, and diarrhea.^[3] When applied to the skin side effects include itchiness, redness, and blisters.^[3] When given by injection there may be fever, liver problems, or hearing loss.^[3] Use during breastfeeding appears to be safe.^[4] Paromomycin is in the aminoglycoside family of medications and causes microbe death by stopping the creation of bacterial proteins.^[3]

Paromomycin was discovered in the 1950s from a type of streptomyces and came into medical use in 1960.^[1]^[4] It is on the World Health Organization's List of Essential Medicines.^[5]^[6] Paromomycin is available as a generic medication.^[7]

^ ^a ^b "Paromomycin". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. 2013. p. 21p. ISBN 978-0-8155-1856-3. Archived from the original on 20 December 2016.
^ Cite error: The named reference Neal1994 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Paromomycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 17 November 2016. Retrieved 3 December 2016.
^ ^a ^b Davidson RN, den Boer M, Ritmeijer K (July 2009). "Paromomycin". Transactions of the Royal Society of Tropical Medicine and Hygiene. 103 (7): 653–660. doi:10.1016/j.trstmh.2008.09.008. PMID 18947845.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 54. ISBN 978-1-284-05756-0.

[Wil2013-1] "Paromomycin". Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. 2013. p. 21p. ISBN 978-0-8155-1856-3. Archived from the original on 20 December 2016.

[Neal1994-2] Cite error: The named reference Neal1994 was invoked but never defined (see the help page).

[AHFS2016-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Paromomycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 17 November 2016. Retrieved 3 December 2016.

[Davidson2008-4] Davidson RN, den Boer M, Ritmeijer K (July 2009). "Paromomycin". Transactions of the Royal Society of Tropical Medicine and Hygiene. 103 (7): 653–660. doi:10.1016/j.trstmh.2008.09.008. PMID 18947845.

[WHO21st-5] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[WHO22nd-6] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[Ric2015-7] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 54. ISBN 978-1-284-05756-0.

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[2]

[3]

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Clinical data


Trade names	Catenulin, Aminosidine, Humatin, others^[1]
Other names	monomycin, aminosidine^[2]
AHFS/Drugs.com	Monograph
MedlinePlus	a601098
License data	US DailyMed: Paromomycin
Pregnancy category	C
Routes of administration	By mouth, intramuscular, topical^[3]
ATC code	A07AA06 (WHO) QJ01GB92 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	Poorly absorbed in the GI tract
Metabolism	Not available
Excretion	Fecal
Identifiers
IUPAC name (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2S,3S,4R,6S)- 4,6-diamino-2-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)- 3-amino-6-(aminomethyl)-4,5-dihydroxy-oxan-2-yl] oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy- 3-hydroxy-cyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol
CAS Number	1263-89-4^Y
PubChem CID	441375
DrugBank	DB01421^Y
ChemSpider	390117^Y
UNII	845NU6GJPS
ChEBI	CHEBI:7934^Y
ChEMBL	ChEMBL370143^N
CompTox Dashboard (EPA)	DTXSID8023424
ECHA InfoCard	100.028.567
Chemical and physical data
Formula	C₂₃H₄₇N₅O₁₈S
Molar mass	713.71 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=S(=O)(O)O.O([C@H]3[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@H]1O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]1N)[C@H]2O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4N)CO
InChI InChI=1S/C23H45N5O14.H2O4S/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1^Y Key:LJRDOKAZOAKLDU-UDXJMMFXSA-N^Y
^NY (what is this?) (verify)

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Paromomycin

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