Phosphate → 2-Hydroxypropanoic acid--3-({3-[(4-aminobutyl)amino]propyl}amino)-7-hydroxycholestan-24-yl hydrogen sulfate (1/1)

HRID 467406Notes

Reaction equation

HRID 467406 reaction equation
[CH3:1][C@@H:2]([C@@H:14]1[C@@:18]2([CH3:43])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:41])[CH2:27][CH2:28][C@H:29]([NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:30][C@@H:25]4[CH2:24][C@@H:23]([OH:42])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:3][CH2:4][C@@H:5]([O:9][S:10]([OH:13])(=[O:12])=[O:11])[CH:6]([CH3:8])[CH3:7].[CH3:44][C@H:45]([OH:49])[C:46]([OH:48])=[O:47].[P:50]([O-:54])([O-:53])([O-:52])=[O:51].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>[CH3:1][C@@H:2]([C@@H:14]1[C@@:18]2([CH3:43])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:41])[CH2:27][CH2:28][C@H:29]([NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:30][C@@H:25]4[CH2:24][C@@H:23]([OH:42])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:3][CH2:4][C@@H:5]([O:9][S:10]([OH:13])(=[O:12])=[O:11])[CH:6]([CH3:7])[CH3:8].[CH3:44][C@H:45]([OH:49])[C:46]([OH:48])=[O:47].[CH3:1][C@@H:2]([C@@H:14]1[C@@:18]2([CH3:43])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:41])[CH2:27][CH2:28][C@H:29]([NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:30][C@@H:25]4[CH2:24][C@@H:23]([OH:42])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:3][CH2:4][C@@H:5]([O:9][S:10]([OH:13])(=[O:12])=[O:11])[CH:6]([CH3:7])[CH3:8].[P:50]([O-:54])([O-:53])([O-:52])=[O:51]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 24243Trisodium PhosphateHCID 30365072-Hydroxypropanoic acid--3-({3-[(4-aminobutyl)amino]propyl}amino)-7-hydroxycholestan-24-yl hydrogen sulfate (1/1)2×

Product 2

HCID 30365072-Hydroxypropanoic acid--3-({3-[(4-aminobutyl)amino]propyl}amino)-7-hydroxycholestan-24-yl hydrogen sulfate (1/1)HCID 86653613HCID 86653613, compound

Reagents, catalysts & solvents 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalSolvent

Procedure

A 10 mg/ml solution of squalamine lactate was prepared in 5% dextrose. A squalamine phosphate suspension was prepared by adjusting the 10 mg/ml squalamine lactate solution to 50 mM phosphate by addition of 1M sodium phosphate, pH 7.4. 0.1 ml of each preparation was then separately injected into the subcutaneous space between the thumb and second finger of a healthy human subject with a syringe bearing a 26 gauge needle. Within seconds of injection of the squalamine lactate solution, the subject experienced an intense stinging sensation not unlike an insect sting. This sensation persisted for about 20 minutes. Over the course of the following 24 hours the site became tender, swollen, and visibly red. These signs and symptoms persisted for about 1 week, gradually diminishing in intensity.

Workup

  1. customsubject with a syringe
  2. customOver the course of the following 24 hours
  3. waitThese signs and symptoms persisted for about 1 week

Sources & evidence

ORD record
ord-6edf2a5ad7274373baa01fed4332c23e
Source dataset
uspto-grants-2014_01
Patent number
US08623416B2

Reaction notes

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