Sarmazenil

Sarmazenil
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QV03AB91 (WHO) ;
Identifiers
	IUPAC name Ethyl 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate;
CAS Number	78771-13-8 ;
PubChem CID	71231;
ChemSpider	64366 ;
UNII	F84AE7X24P;
ChEMBL	ChEMBL46547 ;
CompTox Dashboard (EPA)	DTXSID70229281 ;
Chemical and physical data
Formula	C15H14ClN3O3
Molar mass	319.75 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CC=C3Cl)C;
	InChI InChI=1S/C15H14ClN3O3/c1-3-22-15(21)13-11-7-18(2)14(20)12-9(16)5-4-6-10(12)19(11)8-17-13/h4-6,8H,3,7H2,1-2H3 ; Key:WSDBAFQWNWJTNG-UHFFFAOYSA-N ;
	(what is this?) (verify)

Sarmazenil (Ro15-3505) is a drug from the benzodiazepine family. It acts as a partial inverse agonist of benzodiazepine receptors,^[1] meaning that it causes the opposite effects to most benzodiazepine drugs, and instead acts as an anxiogenic and convulsant. It is used in veterinary medicine to reverse the effects of benzodiazepine sedative drugs in order to rapidly re-awaken anesthetized animals.^[2]^[3]^[4]

References

^ López-Romero B, Evrard G, Durant F, Sevrin M, George P (October 1998). "Molecular structure and stereoelectronic properties of sarmazenil--a weak inverse agonist at the omega modulatory sites (benzodiazepine receptors): comparison with bretazenil and flumazenil". Bioorganic & Medicinal Chemistry. 6 (10): 1745–57. doi:10.1016/S0968-0896(98)00117-5. PMID 9839004.
^ Henke J, Roberts U, Otto K, Lendl C, Matis U, Brill T, Erhardt W (February 1996). "[Clinical investigations of an i.m. combination anesthesia with fentanylclimazolam/xylazine and postoperative i.v. antagonism with naloxone/sarmazenil/yohimbine in guinea pigs]". Tierarztliche Praxis (in German). 24 (1): 85–7. PMID 8720962.
^ Janovsky M, Tataruch F, Ambuehl M, Giacometti M (October 2000). "A Zoletil-Rompun mixture as an alternative to the use of opioids for immobilization of feral red deer". Journal of Wildlife Diseases. 36 (4): 663–9. doi:10.7589/0090-3558-36.4.663. PMID 11085427.
^ Walzer C, Huber C (April 2002). "Partial antagonism of tiletamine-zolazepam anesthesia in cheetah". Journal of Wildlife Diseases. 38 (2): 468–72. doi:10.7589/0090-3558-38.2.468. PMID 12038151.

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[1] López-Romero B, Evrard G, Durant F, Sevrin M, George P (October 1998). "Molecular structure and stereoelectronic properties of sarmazenil--a weak inverse agonist at the omega modulatory sites (benzodiazepine receptors): comparison with bretazenil and flumazenil". Bioorganic & Medicinal Chemistry. 6 (10): 1745–57. doi:10.1016/S0968-0896(98)00117-5. PMID 9839004.

[2] Henke J, Roberts U, Otto K, Lendl C, Matis U, Brill T, Erhardt W (February 1996). "[Clinical investigations of an i.m. combination anesthesia with fentanylclimazolam/xylazine and postoperative i.v. antagonism with naloxone/sarmazenil/yohimbine in guinea pigs]". Tierarztliche Praxis (in German). 24 (1): 85–7. PMID 8720962.

[3] Janovsky M, Tataruch F, Ambuehl M, Giacometti M (October 2000). "A Zoletil-Rompun mixture as an alternative to the use of opioids for immobilization of feral red deer". Journal of Wildlife Diseases. 36 (4): 663–9. doi:10.7589/0090-3558-36.4.663. PMID 11085427.

[4] Walzer C, Huber C (April 2002). "Partial antagonism of tiletamine-zolazepam anesthesia in cheetah". Journal of Wildlife Diseases. 38 (2): 468–72. doi:10.7589/0090-3558-38.2.468. PMID 12038151.

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v t e Benzodiazepines
1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam BMS-906024* Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Cloniprazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Difludiazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine* Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitemazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro05-4082 Ro5-4864* Ro07-5220 Ro07-9749 Ro20-8065 Ro20-8552 SH-I-048A Sulazepam Temazepam Tetrazepam Tifluadom* Timelotem* Tolufazepam Triflunordazepam Tuclazepam Uldazepam
1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam
2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam
Triazolobenzodiazepines	Adinazolam Alprazolam Balovaptan* Bromazolam Clonazolam Estazolam Fluadinazolam Flualprazolam Flubromazolam Flunitrazolam Nitrazolam Phenazolam Pyrazolam Rilmazolam (active metabolite of Rilmazafone) Triazolam
Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil GL-II-73 Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F
Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam
Thienodiazepines	Bentazepam Clotiazepam Ro09-9212
Thienotriazolodiazepines	α-Hydroxyetizolam Apafant* Brotizolam Ciclotizolam Clotizolam Deschloroclotizolam Deschloroetizolam Etizolam Flubrotizolam Fluclotizolam Fluetizolam Israpafant* JQ1* Metizolam
Thienobenzodiazepines*	Olanzapine Telenzepine
Pyridodiazepines	Lopirazepam
Pyridotriazolodiazepines	Zapizolam
Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*
Pyrrolodiazepines	Premazepam
Tetrahydroisoquinobenzodiazepines	Clazolam
Pyrrolobenzodiazepines*	Anthramycin
Benzodiazepine prodrugs	Alprazolam triazolobenzophenone Avizafone Rilmazafone
* atypical activity profile (not GABA_A receptor ligands)

See also

References