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Paromomycin sulfate
Systematic (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
Identifiers
CAS number	1263-89-4
ATC code	A07AA06
PubChem	165580
DrugBank	?
Chemical data
Formula	C₂₃H₄₇N₅O₁₈S
Mol. mass	615.629 g/mol
Pharmacokinetic data
Bioavailability	None
Metabolism	None
Half life	?
Excretion	Fecal
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	Rx only U.S.
Routes	Oral, intramuscular

Paromomycin sulfate (synonyms: monomycin, aminosidine^[1]; brand name Humatin) is an aminoglycoside antibiotic, first isolated from Streptomyces krestomuceticus in 1950s.^[2]

1 Uses
2 Mechanism
3 History and availability
4 References

[edit] Uses

It is an antibiotic designed to fight intestinal infections such as cryptosporidiosis,^[3] amoebiasis,^[4] and leishmaniasis.^[5]

The route of administration is intramuscular injection.

[edit] Mechanism

Paromomycin inhibits protein synthesis by binding to 16S ribosomal RNA.^[6]

[edit] History and availability

Monomycin was demonstrated to be effective against cutaneous leishmaniasis in clinical studies in the USSR in the 1960s, and in trials with visceral leishmaniasis in early 1990s.^[1]

It was developed as a therapeutic against visceral leishmaniasis by the Institute for OneWorld Health. Paromomycin was granted orphan drug status in 2005^[7] and was approved by the Drug Controller General of India in September 2006 for treatment of visceral leishmaniasis.^[8]

As of February 5th, 2008, King Pharmaceuticals is discontinuing the sale of Humatin, Paromomycin continues to be available in the United States from another manufacturer.^[9]

[edit] References

^ ^a ^b Neal R.A. et al. (1994). "Aminosidine ointments for the treatment of experimental cutaneous leishmaniasis". Transactions of the Royal Society of Tropical Medicine and Hygiene 88 (2): 223–5. doi:10.1016/0035-9203(94)90307-7.
^ Davidson R.N., den Boer M., Ritmeijer K. (2008). "Paromomycin". Transactions of the Royal Society of Tropical Medicine and Hygiene. doi:10.1016/j.trstmh.2008.09.008.
^ Sweetman S.C. (Editor). (2002). Martindale: the complete drug reference. 33rd ed. London: Pharmaceutical Press
^ paromomycin at Dorland's Medical Dictionary
^ Sundar S, Jha TK, Thakur CP, Sinha PK, Bhattacharya SK (June 2007). "Injectable paromomycin for visceral leishmaniasis in India". N. Engl. J. Med. 356 (25): 2571–81. doi:10.1056/NEJMoa066536. PMID 17582067. http://content.nejm.org/cgi/pmidlookup?view=short&pmid=17582067&promo=ONFLNS19.
^ Vicens, Quentin; Eric Westhof (August 2001). "Crystal Structure of Paromomycin Docked into the Eubacterial Ribosomal Decoding A Site". Structure 9 (8): 647–658. doi:10.1016/S0969-2126(01)00629-3. PMID 11587639. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VSR-43VBX2W-C&_user=10&_coverDate=08%2F31%2F2001&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=1b1e19d11ca34e14eca1603c2be009d5. Retrieved 2007-02-10.
^ Institute for OneWorld Health (23 May 2005). "Institute for OneWorld Health Drug Receives “Orphan” Designation From U.S. and European Regulatory Agencies". Press release. http://www.oneworldhealth.org/media/details.php?prID=115. Retrieved 2007-02-10.
^ Institute for OneWorld Health (8 September 2006). "New cure for deadly visceral leishmaniasis (kala-azar) approved by government of India". Press release. http://www.oneworldhealth.org/media/details.php?prID=154. Retrieved 2007-02-10.
^ humatin_king.pdf at fda.gov

v • d • e Antidiarrheals, intestinal anti-inflammatory/anti-infective agents (A07)

Intestinal anti-infectives	Antibiotics (Neomycin, Nystatin, Natamycin, Streptomycin, Polymyxin B, Paromomycin, Amphotericin B, Kanamycin, Vancomycin, Colistin, Rifaximin) Sulfonamides (Phthalylsulfathiazole, Sulfaguanidine, Succinylsulfathiazole) Nitrofuran (Nifuroxazide, Nifurzide) Imidazole (Miconazole) Arsenical (Acetarsol) Oxyquinoline (Broxyquinoline)

Intestinal adsorbents	Charcoal · Bismuth · Pectin · Kaolin · Crospovidone · Attapulgite · Diosmectite

Antipropulsives (opioids)	Opium (Laudanum) · Codeine · Morphine (Paregoric) crosses BBB: Diphenoxylate · Difenoxin does not cross BBB: Loperamide

Intestinal anti-inflammatory agents	corticosteroids acting locally (Prednisolone, Hydrocortisone, Prednisone, Betamethasone, Tixocortol, Budesonide, Beclometasone) antiallergic agents, excluding corticosteroids (Cromoglicic acid) aminosalicylic acid and similar agents (Sulfasalazine, Mesalazine, Olsalazine, Balsalazide)

Antidiarrheal micro-organisms	Saccharomyces boulardii

Other antidiarrheals	Albumin tannate · · Octreotide · Ceratonia · Racecadotril

Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)

Entamoeba

Tissue amebicides

Nitroimidazole derivatives	Metronidazole^# · Tinidazole · Ornidazole · Nimorazole · Secnidazole · Azanidazole · Propenidazole

Other	isoquinoline (Emetine/Dehydroemetine)

Luminal amebicides

Hydroxyquinoline derivatives	Cl (Chlorquinaldol) · Br (Tilbroquinol, Broxyquinoline) · I (Diiodohydroxyquinoline) · I,Cl (Clioquinol) related: Chiniofon

Dichloroacetamide derivatives	Diloxanide^# · Clefamide · Etofamide · Teclozan

Aminoglycoside	Paromomycin

Other/ungrouped

arsenic (Arsthinol, Difetarsone, Glycobiarsol) · phenanthroline (Phanquinone) · aminoacridine (Mepacrine) · quinazoline (Trimetrexate) · thiazole (Tenonitrozole) · sesquiterpene (Fumagillin)

Acanthamoeba

Propamidine · Chlorhexidine

^#WHO-EM. ^‡Withdrawn from market. CLINICAL TRIALS: ^†Phase III. ^§Never to phase III
see also diseases

Antiparasitics – antiprotozoal agents – Excavata antiparasitics (P01)

Discicristata

Trypanosomiasis	African trypanosomiasis: ornithine (Eflornithine^#) · arsenical (Melarsoprol^#) · benzamidine (Pentamidine^#) · naphthalenesulfonate (Suramin^#) Chagas disease: nitroimidazole (Benznidazole^#) · nitrofuran (Nifurtimox^#)

Leishmaniasis	macrolide (Amphotericin B^#) Pentavalent antimonials (Meglumine antimoniate^#, Sodium stibogluconate) benzamidine (Pentamidine^#) · phosphorylcholine (Miltefosine) · neomycin (Paromomycin)

PAM	macrolide (Amphotericin B)

Trichozoa

Giardiasis	nitroimidazole (Metronidazole^#, Tinidazole) · benzimidazole (Albendazole) thiazole (Nitazoxanide) · nitrofuran (Furazolidone) aminoacridine (Quinacrine)

Trichomoniasis	nitroimidazole (Metronidazole^#, Tinidazole)

Dientamoebiasis	nitroimidazole (Metronidazole, Secnidazole) oxyquinoline (Iodoquinol) · tetracycline (Doxycycline) · neomycin (Paromomycin)

^#WHO-EM. ^‡Withdrawn from market. CLINICAL TRIALS: ^†Phase III. ^§Never to phase III
see also diseases

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin Neomycin (Framycetin, Paromomycin, Ribostamycin) Kanamycin (Amikacin, Arbekacin, Bekanamycin, Dibekacin, Tobramycin) Spectinomycin^# · Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# (Netilmicin, Sisomicin, Isepamicin) Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# •Chlortetracycline • Clomocycline • Demeclocycline • Lymecycline • Meclocycline • Metacycline • Minocycline • Oxytetracycline • Penimepicycline • Rolitetracycline • Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Linezolid • Torezolid

Peptidyl transferase

Amphenicols	Chloramphenicol^# · Azidamfenicol · Thiamphenicol · Florfenicol

Pleuromutilins	Retapamulin · Tiamulin · Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Erythromycin^# · Azithromycin^# · Spiramycin · Midecamycin · Oleandomycin · Roxithromycin · Josamycin · Troleandomycin · Clarithromycin · Miocamycin · Rokitamycin · Dirithromycin · Flurithromycin · Ketolide (Telithromycin, Cethromycin)

Lincosamides	Clindamycin^# · Lincomycin

Streptogramins	Pristinamycin · Quinupristin/dalfopristin · Virginiamycin

EF-G

Steroid antibacterials

Fusidic acid

^#WHO-EM. ^‡Withdrawn from market. CLINICAL TRIALS: ^†Phase III. ^§Never to phase III

Types of Carbohydrates

General:

Aldose · Ketose · Pyranose · Furanose

Geometry

Cyclohexane conformation · Anomer · Mutarotation

Monosaccharides

Trioses	Ketotriose (Dihydroxyacetone) · Aldotriose (Glyceraldehyde)

Tetroses	Ketotetrose (Erythrulose) · Aldotetroses (Erythrose, Threose)

Pentoses	Ketopentose (Ribulose, Xylulose) Aldopentose (Ribose, Arabinose, Xylose, Lyxose) Deoxy sugar (Deoxyribose)

Hexoses	Ketohexose (Psicose, Fructose, Sorbose, Tagatose) Aldohexose (Allose, Altrose, Glucose, Mannose, Gulose, Idose, Galactose, Talose) Deoxy sugar (Fucose, Fuculose, Rhamnose)

>6	Heptose (Sedoheptulose) · Octose · Nonose (Neuraminic acid)

Multiple

Disaccharides	Sucrose · Lactose · Maltose · Trehalose · Turanose · Cellobiose

Trisaccharides	Raffinose · Melezitose · Maltotriose

Tetrasaccharides	Acarbose · Stachyose

Other oligosaccharides	Fructooligosaccharide (FOS) · Galactooligosaccharides (GOS) · Mannan-oligosaccharides (MOS)

Polysaccharides	Glucose/Glucan: Glycogen · Starch (Amylose, Amylopectin) · Cellulose · Dextrin/Dextran · Beta-glucan (Zymosan, Lentinan, Sizofiran) · Maltodextrin Fructose/Fructan: Inulin · Levan beta 2→6 Mannose/Mannan Galactose/Galactan N-Acetylglucosamine: Chitin