Paromomycin
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| Category | Antibiotics |
| Catalog number | BBF-00497 |
| CAS | 7542-37-2 |
| Molecular Weight | 615.63 |
| Molecular Formula | C23H45N5O14 |
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Description
It is produced by the strain of Streptomyces rimosus var. paromomycinus. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis. It has a role as an antibacterial drug, an antiprotozoal drug, an anthelminthic drug and an antiparasitic agent.
Specification
| Related CAS | 1263-89-4 (sulfate) 35665-49-7 (sulfate (2:5)) 7205-49-4 (sulfate (1:1)) |
| Synonyms | Catenulin; Aminosidin; AMINOSIDINE; Hydroxymycin; Zygomycin A1; Crestomycin; Paucimycin; Estomycin; Monomycin A; Paromomycin I |
| IUPAC Name | (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N |
| InChI | InChI=1S/C23H45N5O14/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/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1 |
| InChI Key | UOZODPSAJZTQNH-LSWIJEOBSA-N |
Properties
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 658.93 °C (Predicted) |
| Density | 1.375 g/cm3 (Predicted) |
Reference Reading
1.Treatment of Cutaneous Leishmaniasis Caused by Leishmania aethiopica: A Systematic Review.
van Griensven J1, Gadisa E2, Aseffa A2, Hailu A3, Beshah AM4, Diro E5. PLoS Negl Trop Dis. 2016 Mar 3;10(3):e0004495. doi: 10.1371/journal.pntd.0004495. eCollection 2016.
Leishmania aethiopica is the etiological agent of cutaneous leishmaniasis (CL) in Ethiopia and can cause severe and complicated cases such as diffuse CL (DCL), mucocutaneous leishmaniasis or extensive CL, requiring systemic treatment. Despite the substantial burden, evidence-based treatment guidelines are lacking. We conducted a systematic review of clinical studies reporting on treatment outcomes of CL due to L aethiopica in order to help identify potentially efficacious medications on CL that can be taken forward for clinical trials. We identified a total of 24 records reporting on 506 treatment episodes of CL presumably due to L aethiopica. The most commonly used drugs were antimonials (n = 201), pentamidine (n = 150) and cryotherapy (n = 103). There were 20 case reports/series, with an overall poor study quality. We only identified two small and/or poor quality randomized controlled trials conducted a long time ago. There were two prospective non-randomized studies reporting on cryotherapy, antimonials and pentamidine.
2.Solid lipid nanoparticle loaded with paromomycin: in vivo efficacy against Leishmania tropica infection in BALB/c mice model.
Heidari-Kharaji M1, Taheri T1, Doroud D2, Habibzadeh S1, Rafati S3. Appl Microbiol Biotechnol. 2016 Mar 10. [Epub ahead of print]
Leishmaniasis is a parasitic disease transmitted through the bite of an infected phlebotomine sand fly and caused by protozoan parasites of the genus Leishmania. There is no available vaccine for leishmaniasis in human, and the current chemotherapy approaches are hampered by different clinical problems. Most of available drugs are confined to a limited number of toxic chemical compounds, which some parasite strains have evolved drug resistance against. Hence, drug discovery and production of a new anti leishmanial compound is essential. One promising strategy is using the nanoparticle delivery systems with the aim of accelerating the efficacy of the available treatments. In the present study, paromomycin sulfate (PM) was formulated in solid lipid nanoparticles (SLN) and the in vivo efficacy was investigated against Leishmania tropica in BALB/c mice model. To do so, the increase in footpad thickness was measured and real-time PCR was performed to quantify the parasite load after infectious challenge.
3.What a Difference an OH Makes: Conformational Dynamics as the Basis for the Ligand Specificity of the Neomycin-Sensing Riboswitch.
Duchardt-Ferner E1, Gottstein-Schmidtke SR1, Weigand JE2, Ohlenschläger O3, Wurm JP1, Hammann C4, Suess B2, Wöhnert J5. Angew Chem Int Ed Engl. 2016 Jan;55(4):1527-30. doi: 10.1002/anie.201507365. Epub 2015 Dec 11.
To ensure appropriate metabolic regulation, riboswitches must discriminate efficiently between their target ligands and chemically similar molecules that are also present in the cell. A remarkable example of efficient ligand discrimination is a synthetic neomycin-sensing riboswitch. Paromomycin, which differs from neomycin only by the substitution of a single amino group with a hydroxy group, also binds but does not flip the riboswitch. Interestingly, the solution structures of the two riboswitch-ligand complexes are virtually identical. In this work, we demonstrate that the local loss of key intermolecular interactions at the substitution site is translated through a defined network of intramolecular interactions into global changes in RNA conformational dynamics. The remarkable specificity of this riboswitch is thus based on structural dynamics rather than static structural differences. In this respect, the neomycin riboswitch is a model for many of its natural counterparts.
4.Drug permeation and barrier damage in Leishmania-infected mouse skin.
Van Bocxlaer K1, Yardley V2, Murdan S3, Croft SL4. J Antimicrob Chemother. 2016 Feb 21. pii: dkw012. [Epub ahead of print]
OBJECTIVES: Pathological disorder can disrupt the barrier integrity of the skin, thereby altering the drug delivery from topical formulations to the target site. Cutaneous leishmaniasis (CL) is an infection of the dermal layers of the skin and manifests as a variety of skin lesions from defined nodular forms to plaques and chronic ulcers. The aim of this work was to characterize the physiology and barrier integrity of the Leishmania-infected BALB/c mouse skin and how they impacted delivery of drugs into the skin.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
