The length of the migrating MMC cycle is prolonged by L-Hyoscyamine (Daturine; 5–20 mg/kg; IV)[1].

Animal/Disease Models: Rats[1]
Doses: 5, 10, 20 mg/kg
Route of Administration: IV
Experimental Results: Prolonged the migrating myoelectric complex (MMC) cycle length.

Absorption, Distribution and Excretion
Hyoscyamine is completely absorbed by sublingual and oral routes, though exact data regarding the Cmax, Tmax, and AUC are not readily available.
The majority of hyoscyamine is eliminated in the urine as the unmetabolized parent compound.

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Metabolism / Metabolites
Hyoscyamine is largely unmetabolized, however a small amount is hydrolyzed into tropine and tropic acid.
LIVER HOMOGENATES OF RABBITS CONTAINING (-)-HYOSCYAMINE ACYLHYDROLASE HYDROLYZED (-)-HYOSCYAMINE TO TROPINE AND(-)-TROPIC ACID BUT DID NOT CLEAVE (+)-HYOSCYAMINE.

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Biological Half-Life
The half life of hyoscyamine is 3.5 hours.

Hepatotoxicity
Despite widespread use over many decades, hyoscyamine has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. A major reason for its safety may relate to the low daily dose and limited duration of use.
References on the safety and potential hepatotoxicity of anticholinergics are given together after the Overview section on Anticholinergic Agents.
Drug Class: Gastrointestinal Agents; Anticholinergic Agents

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Interactions
L-HYOSCYAMINE (0.3 MG/KG) PREVENTED THE SALIVATION INDUCED IN MICE BY CHOLINERGIC AND ADRENERGIC DRUGS WITHOUT AFFECTING THE ACCOMPANYING TEMP RESPONSES. WHEN GIVEN 30 MIN BEFORE THE INJECTION OF AN ADRENERGIC SIALAGOGUE, IT DID NOT INHIBIT THE SALIVATION INDUCED BY D-AMPHETAMINE SULFATE BUT STILL DIMINISHED THAT CAUSED BY L-ISOPROTERENOL BITARTRATE.

[1]. Regulatory role of 5-HT and muscarinic receptor antagonists on the migrating myoelectric complex in rats. Eur J Pharmacol. 2003 Apr 25;467(1-3):211-8.

[2]. Application of an enantioselective LC-ESI MS/MS procedure to determine R- and S-hyoscyamine following intravenous atropine administration in swine. Drug Test Anal. Mar-Apr 2012;4(3-4):194-8.

(S)-atropine is an atropine with a 2S-configuration. It is functionally related to a (S)-tropic acid. It is a conjugate base of a (S)-atropinium.
Hyoscyamine is a tropane alkaloid and the levo-isomer of [atropine]. It is commonly extracted from plants in the Solanaceae or nightshade family. Research into the action of hyoscyamine in published literature dates back to 1826. Hyoscyamine is used for a wide variety of treatments and therapeutics due to its antimuscarinic properties. Although hyoscyamine is marketed in the United States, it is not FDA approved.
Hyoscyamine as a natural plant alkaloid derivative and anticholinergic that is used to treat mild to moderate nausea, motion sickness, hyperactive bladder and allergic rhinitis. Hyoscyamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
L-Hyoscyamine has been reported in Scopolia parviflora, Cyphanthera odgersii, and other organisms with data available.
Hyoscyamine is a belladonna alkaloid derivative and the levorotatory form of racemic atropine isolated from the plants Hyoscyamus niger or Atropa belladonna, which exhibits anticholinergic activity. Hyoscyamine functions as a non-selective, competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary, bronchial, and sweat glands, as well as the eye, heart, bladder, and gastrointestinal tract. These inhibitory effects cause a decrease in saliva, bronchial mucus, gastric juices, and sweat. Furthermore, its inhibitory action on smooth muscle prevents bladder contraction and decreases gastrointestinal motility.
The 3(S)-endo isomer of atropine.
See also: Atropine (annotation moved to); Hyoscyamine (annotation moved to).

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Drug Indication
As a drug that is not FDA approved, hyscyamine has no official indications. Intravenous hysocyamine has been used to reduce gastric motility, reduce pancreatic pain and secretions, to facilitate imaging of the gastrointestinal tract, treat anticholinesterase toxicity, treat certain cases of partial heart block, improve visualization of the kidneys, and for symptomatic relief of biliary and renal colic. Intravenous hyoscyamine is also used pre-operatively to reduce secretions of the mouth and respiratory tract to facilitate intubation. Oral hyoscyamine is used to treat functional intestinal disorders, for symptomatic relief of biliary and renal colic, and symptomatic relief of acute rhinitis.

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Mechanism of Action
Hyoscyamine competitively and non-selectively antagonises muscarinic receptors in the smooth muscle, cardiac muscle, sino-atrial node, atrioventricular node, exocrine nodes, gastrointestinal tract, and respiratory tract. Antagonism of muscarinic M1, M4, and M5 receptors in the central nervous system lead to cognitive impairment; antagonism of M2 in the sinoatrial and atrioventricular nodes leads to increases in heart rate and atrial contractility; and antagonism of M3 in smooth muscle results in reduced peristalsis, bladder contraction, salivary secretions, gastric secretions, bronchial secretions, sweating, increased bronchodilation, mydriasis, and cycloplegia.
MAJOR ACTION OF ANTIMUSCARINIC AGENTS IS A COMPETITIVE ANTAGONISM OF THE ACTIONS OF ACETYLCHOLINE & OTHER MUSCARINIC AGONISTS. ... RECEPTORS AFFECTED ARE THOSE OF PERIPHERAL STRUCTURES THAT ARE...STIMULATED OR INHIBITED BY MUSCARINE, THAT IS, EXOCRINE GLANDS & SMOOTH & CARDIAC MUSCLE. RESPONSES TO POSTGANGLIONIC CHOLINERGIC NERVE STIMULATION ARE ALSO INHIBITED...BUT LESS READILY THAN RESPONSES TO INJECTED CHOLINE ESTERS. /ANTIMUSCARINIC DRUGS/

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Therapeutic Uses
Adjuvants, Anesthesia; Anti-Arrhythmia Agents; Antidotes; Bronchodilator Agents; Muscarinic Antagonists; Mydriatics; Parasympatholytics
/L-HYOSCYAMINE IS/ THE LEVOROTATORY ISOMER OF THE RACEMIC MIXTURE.../DL-ATROPINE/, & THEREFORE 1/2 OF ATROPINE IS HYOSCYAMINE. SINCE DEXTROROTATORY ISOMER IS NEARLY INACTIVE, THE POTENCY OF HYOSCYAMINE IS APPROX TWICE THAT OF ATROPINE. ACTIONS /&/ USES...ARE SAME AS THOSE OF ANTIMUSCARINIC DRUGS IN GENERAL, EXCEPT THAT HYOSCYAMINE HAS NOT BEEN USED FOR OPHTHALMOLOGIC PURPOSES & IS OF LITTLE USE TO SUPPRESS GASTRIC SECRETION. ...ITS USE HAS MAINLY BEEN CONFINED TO THAT OF AN ANTISPASMODIC.
TEN MALE PATIENTS WITH CHRONIC DUODENAL ULCERATION WERE EXAMINED WITH AN AUGMENTED HISTAMINE TEST BEFORE AND DURING TREATMENT WITH OPTIMAL EFFECTIVE DOSES OF LONG-ACTING L-HYOSCYAMINE 0.84 MG, GIVEN 3 TIMES DAILY. ACID OUTPUT WAS STIMULATED AND SECRETORY VOLUME WAS SIGNIFICANTLY REDUCED DURING TREATMENT, WHILE THE PEPSIN AND INTRINSIC FACTOR SECRETION WERE UNALTERED.
IN HEALTHY VOLUNTEERS L-HYOSCYAMINE (0.6 MG, TWICE A DAY) AFFECTED SALIVARY SECRETION SIGNIFICANTLY. GASTRIC EMPTYING WAS SIGNIFICANTLY DELAYED BY L-HYOSCYAMINE COMPARED TO PIRENZEPINE. SWALLOWING-INDUCED ESOPHAGEAL PERISTALSIS WAS INHIBITED IN 51% BY L-HYOSCYAMINE. IT ALSO AFFECTED BOTH PUPIL-SIZE AND NEARPOINT DISTANCE.
For more Therapeutic Uses (Complete) data for (-)-HYOSCYAMINE (6 total), please visit the HSDB record page.

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Pharmacodynamics
Hyoscyamine is not FDA approved, and so it has not official indications. However, it is used as an antimuscarinic agent in a number of treatments and therapies. Hyoscyamine has a short duration of action as it may need to be given multiple times per day. Patients should be counselled regarding the risks and signs of anticholinergic toxicity.

C17H23NO3

289.37

289.167

101-31-5

L-Hyoscyamine sulfate;620-61-1;L-Hyoscyamine-d3

154417

White to off-white solid powder

1.2±0.1 g/cm3

429.8±45.0 °C at 760 mmHg

108.5ºC

213.7±28.7 °C

0.0±1.1 mmHg at 25°C

1.581

1.53

1

4

5

21

353

3

CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)[C@H](CO)C3=CC=CC=C3

RKUNBYITZUJHSG-VFSICIBPSA-N

InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m1/s1

[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (8.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 30% Propylene glycol , 5% Tween 80 , 65% D5W: 5 mg/mL

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 (Please use freshly prepared in vivo formulations for optimal results.)