Sugammadex

Sugammadex

Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: Bridion
Routes of administration	Intravenous
ATC code	V03AB35 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Identifiers
CAS Number	343306-79-6 N
PubChem CID	6918584
ChemSpider	5293781 N
UNII	361LPM2T56
KEGG	D05940 Y
ChEBI	CHEBI:90952 N
Chemical and physical data
Formula	C72H104Na8O48S8
Molar mass	2178 g/mol
3D model (Jmol)	Interactive image
SMILES [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O=C([O-])CCSC[C@H]8O[C@@H]7O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@@H]1CSCCC(=O)[O-])O[C@H]2[C@H](O)[C@@H](O)[C@H](O[C@@H]2CSCCC(=O)[O-])O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3CSCCC(=O)[O-])O[C@H]4[C@H](O)[C@@H](O)[C@H](O[C@@H]4CSCCC(=O)[O-])O[C@@H]9[C@H](O[C@H](O[C@H]5[C@H](O)[C@@H](O)[C@H](O[C@@H]5CSCCC(=O)[O-])O[C@H]6[C@H](O)[C@@H](O)[C@H](O[C@@H]6CSCCC([O-])=O)O[C@H]8[C@H](O)[C@H]7O)[C@H](O)[C@H]9O)CSCCC(=O)[O-]
InChI InChI=1S/C72H112O48S8.8Na/c73-33(74)1-9-121-17-25-57-41(89)49(97)65(105-25)114-58-26(18-122-10-2-34(75)76)107-67(51(99)43(58)91)116-60-28(20-124-12-4-36(79)80)109-69(53(101)45(60)93)118-62-30(22-126-14-6-38(83)84)111-71(55(103)47(62)95)120-64-32(24-128-16-8-40(87)88)112-72(56(104)48(64)96)119-63-31(23-127-15-7-39(85)86)110-70(54(102)46(63)94)117-61-29(21-125-13-5-37(81)82)108-68(52(100)44(61)92)115-59-27(19-123-11-3-35(77)78)106-66(113-57)50(98)42(59)90;;;;;;;;/h25-32,41-72,89-104H,1-24H2,(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,83,84)(H,85,86)(H,87,88);;;;;;;;/q;8*+1/p-8/t25-,26-,27-,28-,29-,30-,31-,32-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-;;;;;;;;/m1......../s1 N Key:KMGKABOMYQLLDJ-VKHHSAQNSA-F N
NY (what is this?)

Sugammadex (Org 25969, tradename Bridion) is an agent for reversal of neuromuscular blockade by the agent rocuronium in general anaesthesia. It is the first selective relaxant binding agent (SRBA).

Sugammadex is used to reverse neuromuscular blockade after administration of non-depolarizing neuromuscular-blocking agents such as vecuronium or rocuronium.

Sugammadex is a modified γ-cyclodextrin, with a lipophilic core and a hydrophilic periphery. This gamma cyclodextrin has been modified from its natural state by placing eight carboxyl thio ether groups at the sixth carbon positions. These extensions extend the cavity size allowing greater encapsulation of the rocuronium molecule. These negatively charged extensions electrostatically bind to the quaternary nitrogen of the target as well as contribute to the aqueous nature of the cyclodextrin. Sugammadex's binding encapsulation of rocuronium is one of the strongest among cyclodextrins and their guest molecules. The rocuronium molecule (a modified steroid) bound within sugammadex's lipophilic core, is rendered unavailable to bind to the acetylcholine receptor at the neuromuscular junction.

Sugammadex, unlike neostigmine, does not inhibit acetylcholinesterase so cholinergic effects are not produced and co-administration of an antimuscarinic agent (glycopyrronium bromide or atropine) is not needed. Sugammadex might therefore be expected to have fewer adverse effects than the traditional reversal agents.