Capreomycin

{{Short description|Pharmaceutical drug}} {{Use dmy dates|date=October 2025}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | image = Capreomycin IA.svg | image_class = skin-invert-image | alt = | image2 = Capreomycin IB.svg | image_class2 = skin-invert-image | alt2 =

| pronounce = | tradename = Capastat | Drugs.com = {{drugs.com|monograph|capreomycin-sulfate}} | MedlinePlus = a682860 | DailyMedID =  | pregnancy_AU =  | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intramuscular | class = | ATC_prefix = J04 | ATC_suffix = AB30 | ATC_supplemental =

| IUPAC_name = (3''S'')-3,6-diamino-''N''-<nowiki>[[</nowiki>(2''S'',5''S'',8''E'',11''S'',15''S'')-15-amino-11-[(4''R'')-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide; (3''S'')-3,6-diamino-''N''-<nowiki>[[</nowiki>(2''S'',5''S'',8''E'',11''S'',15''S'')-15-amino-11-[(4''R'')-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide | C=25 | H=44 | N=14 | O=8 | SMILES = C[C@H]1C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)[C@H]2CCN=C(N2)N)CNC(=O)C[C@H](CCCN)N.C1CN=C(N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N2)CNC(=O)C[C@H](CCCN)N)CO)N)N | StdInChI = 1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9+;16-10+/t11-,12-,13+,14-,16-,18-;11-,12-,13-,14+,15-,18-/m00/s1 | StdInChIKey = VCOPTHOUUNAYKQ-WBTCAYNUSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

'''Capreomycin''' is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis.<ref name="AHFS2016" /> Specifically it is a second line treatment used for active drug resistant tuberculosis.<ref name="AHFS2016" /> It is given by injection into a vein or muscle.<ref name=AHFS2016>{{cite web | title = Capreomycin Sulfate | url = https://www.drugs.com/monograph/capreomycin-sulfate.html | publisher = The American Society of Health-System Pharmacists | access-date = 8 December 2016 | url-status = live | archive-url = https://web.archive.org/web/20161220231143/https://www.drugs.com/monograph/capreomycin-sulfate.html | archive-date = 20 December 2016 }}</ref>

Common side effects include kidney problems, hearing problems, poor balance, and pain at the site of injection.<ref name="AHFS2016" /> Other side effects include paralysis resulting in the inability to breathe.<ref name="AHFS2016" /> It is not recommended with streptomycin or other medications that may damage the auditory vestibular nerve.<ref name="AHFS2016" /> It is not recommended during pregnancy as it may cause kidney or hearing problems in the baby.<ref name="AHFS2016" /> Capreomycin is commonly grouped with the aminoglycoside family of medications.<ref>{{cite book | vauthors = Navneet K | title = Textbook of Neurology | pages = 192 | date = 2015 | publisher = PHI Learning Pvt. Ltd. | isbn = 978-81-203-4243-9 | url = https://books.google.com/books?id=gm_W3r91J0YC&pg=PA192 | language = en | url-status = live | archive-url = https://web.archive.org/web/20161220090022/https://books.google.ca/books?id=gm_W3r91J0YC&pg=PA192 | archive-date = 20 December 2016 }}</ref> How it works is unclear.<ref name="AHFS2016" />

Capreomycin was discovered from ''Streptomyces capreolus'' in 1960.<ref>{{cite web | vauthors = Tomlinson C | title = TB Online – Capreomycin | url = http://www.tbonline.info/posts/2011/8/23/capreomycin/ | access-date = 14 September 2014 | url-status = live | archive-url = https://web.archive.org/web/20150113184425/http://www.tbonline.info/posts/2011/8/23/capreomycin/ | archive-date = 13 January 2015 }}</ref> It was removed from the World Health Organization's List of Essential Medicines in 2019.<ref name="World_Health_Organization_2019">{{cite book | vauthors = ((World Health Organization)) | title = Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines | location = Geneva | year = 2019 | publisher = World Health Organization | author-link = World Health Organization | hdl = 10665/325773 | id = WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO | hdl-access = free }}</ref>

==Spectrum of susceptibility== Capreomycin is most commonly used to treat ''Mycobacterium tuberculosis'' infections. ''Mycobacterium tuberculosis'' growth has been found to be inhibited at a concentration of 2.5 μg/mL.<ref name="m495">{{cite web | title = Mycobacterium tuberculosis (BACTEC 460 H37Ra) | website = TOKU-E | url = https://antibiotics.toku-e.com/microorganism_detail_7867.html | access-date = 13 June 2024 }}</ref>

== Side effects == {{unreferenced section|date=September 2019}} High incidence: hematuria, urine output or urinary frequency significantly increased or decreased, loss of appetite or extreme thirst (hypokalemia, renal toxicity).

Less incidence: hearing loss, tinnitus, gait instability, dizziness, dyspnea, lethargy, extreme weakness (neuromuscular blockade, renal toxicity, hypokalemia), nausea or vomiting.<ref>{{cite journal | vauthors = Shibeshi W, Sheth AN, Admasu A, Berha AB, Negash Z, Yimer G | title = Nephrotoxicity and ototoxic symptoms of injectable second-line anti-tubercular drugs among patients treated for MDR-TB in Ethiopia: a retrospective cohort study | journal = BMC Pharmacology & Toxicology | volume = 20 | issue = 1 | article-number = 31 | date = May 2019 | pmid = 31122273 | pmc = 6533713 | doi = 10.1186/s40360-019-0313-y | doi-access = free }}</ref>

Significant renal toxicity: blood creatinine increase, blood urea nitrogen increase, poor creatinine clearance, proteinuria (need routine blood monitoring of renal functions and urine analysis) during usage of this medication.

Damaging to the 8th cranial nerve . There can be vestibular dysfunction, such as some minor hearing loss after using the medication for 2 to 4 months.

A certain block effect of neuromuscular.

Can cause allergic reactions: rash, drug fever, facial flushing or pale, asthma, palpitations, sense of suppression in the chest, abdominal pain, anaphylactic shock.

== Interactions == {{unreferenced section|date=September 2019}} Combined with an aminoglycoside, it can increase the possibility of ototoxicity, nephrotoxicity and neuromuscular blockage, result in some hearing loss or can continue to deafness. It could be a temporary symptom, but often be permanent. Neuromuscular blockade can lead to skeletal muscle weakness and respiratory depression or paralysis (apnea). Using anti-cholinesterase or calcium salts may release this block.

Combined with amphotericin B, vancomycin, bacitracin, paromomycin, cyclosporine, kanamycin, cisplatin, bumetanide, etoricoxib, furosemide: Would Increase the possibility of ototoxicity and nephrotoxicity.

Combined with antihistamines, buclizine, cyclizine, meclizine, phenothiazines, thioketones, trimethamine, and capreomycin: can ameliorate the symptoms of tinnitus, dizziness or vertigo and other ototoxic symptoms.

Combined with anti-neuromuscular block drugs: can antagonize the effect of the anti-neuromuscular block drugs on the skeletal muscle (so need to adjust the dose of the drugs for anti-muscle weakness.

Combined with ethyl sulfide isoniazid: may increase the side effects.

Combined with methoxyflurane or polymyxin injection: may increase renal toxicity or neuromuscular blockade effect.

Combined with opioid: The effect of central respiratory inhibition may increase, lead to prolonged respiratory inhibition or respiratory paralysis (apnea).

== History ==

Capreomycin, an antiphlogistic antibiotic which was produced in the United States in 1960, and be applied in clinic in 1968. In 1979, capreomycin was used in the area of antituberculosis by inhibiting the growth of ''Mycobacterium tuberculosis''.{{citation needed|date=August 2022}}

== References == {{Reflist}}

Category:Wikipedia medicine articles ready to translate Category:Anti-tuberculosis drugs Category:Polypeptide antibiotics